What is the best way to travel from Mississauga, ON to Chicago?
Looking for a trip? Check and compare all the available Flights and Buses to Chicago from Mississauga, ON. Look at different modes of transportation, search for the cheapest tickets, fastest rides and most popular stations, and see all 1 available companies to find your perfect trip!
What is the cheapest way to reach Chicago from Mississauga, ON?
You can reach Chicago with just £47 by taking a Bus from FlixBus, but there are many more cheap offers: we have selected the best ones for you for the next few days here.
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FlixBus19h 50m010:35Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/04/2026 05:25:00. 50 Economy ticket for £47 per person are available. Travel duration is 19h 50m
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FlixBus22h 45m010:35Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 22/04/2026 08:20:00. 50 Economy ticket for £49 per person are available. Travel duration is 22h 45m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £93 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m009:25Pearson Toronto AirportPearson Toronto Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £93 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £106 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m008:10Pearson Toronto AirportPearson Toronto Airport09:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 08:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 09:10:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Skyscanner1h 55m018:30Pearson Toronto AirportPearson Toronto Airport19:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 18:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 19:25:00. 50 Economy ticket for £116 per person are available. Travel duration is 1h 55m
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Flair Airlines15h 47m006:30Pearson Toronto AirportPearson Toronto Airport21:17Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 06:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 21:17:00. 50 Economy ticket for £132 per person are available. Travel duration is 15h 47m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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FlixBus19h 50m002:35Pearson Toronto AirportPearson Toronto Airport21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/04/2026 21:25:00. 50 Economy ticket for £63 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/04/2026 05:25:00. 50 Economy ticket for £63 per person are available. Travel duration is 19h 50m
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FlixBus22h 0m002:35Pearson Toronto AirportPearson Toronto Airport23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 22/04/2026 23:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 22h 0m
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FlixBus22h 45m010:35Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 23/04/2026 08:20:00. 50 Economy ticket for £77 per person are available. Travel duration is 22h 45m
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Air Canada1h 55m008:15Pearson Toronto AirportPearson Toronto Airport09:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 08:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/04/2026 09:10:00. 50 Economy ticket for £115 per person are available. Travel duration is 1h 55m
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Flair Airlines29h 42m010:05Pearson Toronto AirportPearson Toronto Airport14:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:05:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 14:47:00. 50 Economy ticket for £184 per person are available. Travel duration is 29h 42m
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Porter Airlines29h 42m010:05Pearson Toronto AirportPearson Toronto Airport14:47Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 14:47:00. 50 Economy ticket for £200 per person are available. Travel duration is 29h 42m
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Flair Airlines18h 54m006:30Pearson Toronto AirportPearson Toronto Airport00:24Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 06:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 00:24:00. 50 Economy ticket for £209 per person are available. Travel duration is 18h 54m
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Skyscanner2h 3m011:00Pearson Toronto AirportPearson Toronto Airport12:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/04/2026 12:03:00. 50 Economy ticket for £221 per person are available. Travel duration is 2h 3m
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United Airlines2h 3m007:00Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 07:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/04/2026 08:03:00. 50 Economy ticket for £221 per person are available. Travel duration is 2h 3m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 24/04/2026 05:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 17h 40m
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FlixBus20h 35m012:45Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 24/04/2026 08:20:00. 50 Economy ticket for £73 per person are available. Travel duration is 20h 35m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 24/04/2026 11:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 12h 50m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 10:15:00. 50 Economy ticket for £89 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 10:15:00. 50 Economy ticket for £91 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m016:50Pearson Toronto AirportPearson Toronto Airport17:50Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 16:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 17:50:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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CargoLogicAir6h 15m007:45Pearson Toronto AirportBilly Bishop Toronto City Airport13:00Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/04/2026 07:45:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 13:00:00. 50 Economy ticket for £136 per person are available. Travel duration is 6h 15m
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Skyscanner2h 10m006:15Pearson Toronto AirportPearson Toronto Airport07:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 06:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 07:25:00. 50 Economy ticket for £143 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m006:15Pearson Toronto AirportPearson Toronto Airport07:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 06:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 07:25:00. 50 Economy ticket for £145 per person are available. Travel duration is 2h 10m
Cheapest Buses Thursday
Cheapest Flights Thursday
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 12h 50m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 24/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 12h 30m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 40m
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Air Canada2h 0m012:05Pearson Toronto AirportPearson Toronto Airport13:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/04/2026 13:05:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Allegiant Air22h 36m012:00Pearson Toronto AirportBilly Bishop Toronto City Airport09:36Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 12:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 09:36:00. 50 Economy ticket for £158 per person are available. Travel duration is 22h 36m
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Porter Airlines31h 16m010:05Pearson Toronto AirportPearson Toronto Airport16:21Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 10:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 16:21:00. 50 Economy ticket for £159 per person are available. Travel duration is 31h 16m
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CargoLogicAir1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £178 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £211 per person are available. Travel duration is 1h 50m
Cheapest Buses Friday
Cheapest Flights Friday
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 17:35:00. 50 Economy ticket for £65 per person are available. Travel duration is 16h 0m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 40m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 25/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 11:25:00. 50 Economy ticket for £68 per person are available. Travel duration is 12h 30m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 11:25:00. 50 Economy ticket for £69 per person are available. Travel duration is 12h 50m
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CargoLogicAir1h 50m011:20Pearson Toronto AirportBilly Bishop Toronto City Airport12:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 25/04/2026 11:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 12:10:00. 50 Economy ticket for £88 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m011:20Pearson Toronto AirportBilly Bishop Toronto City Airport12:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 25/04/2026 11:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 12:10:00. 50 Economy ticket for £91 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m014:15Pearson Toronto AirportPearson Toronto Airport15:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 14:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 15:15:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m014:15Pearson Toronto AirportPearson Toronto Airport15:15Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 14:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 15:15:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m017:50Pearson Toronto AirportPearson Toronto Airport18:53Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 17:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 18:53:00. 50 Economy ticket for £116 per person are available. Travel duration is 2h 3m
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United Airlines2h 3m017:50Pearson Toronto AirportPearson Toronto Airport18:53Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 17:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 18:53:00. 50 Economy ticket for £118 per person are available. Travel duration is 2h 3m
Cheapest Buses Saturday
Cheapest Flights Saturday
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 05:25:00. 50 Economy ticket for £66 per person are available. Travel duration is 17h 40m
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 17:35:00. 50 Economy ticket for £70 per person are available. Travel duration is 16h 0m
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FlixBus20h 35m012:45Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 27/04/2026 08:20:00. 50 Economy ticket for £73 per person are available. Travel duration is 20h 35m
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FlixBus15h 25m002:35Pearson Toronto AirportPearson Toronto Airport17:00Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 26/04/2026 17:00:00. 50 Economy ticket for £75 per person are available. Travel duration is 15h 25m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 11:25:00. 50 Economy ticket for £76 per person are available. Travel duration is 12h 50m
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Porter Airlines1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 26/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/04/2026 15:20:00. 50 Economy ticket for £96 per person are available. Travel duration is 1h 50m
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Spirit Airlines2h 0m008:50Pearson Toronto AirportPearson Toronto Airport09:50Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 08:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 09:50:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Delta Air Lines3h 59m009:46Pearson Toronto AirportPearson Toronto Airport12:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 09:46:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 12:45:00. 50 Economy ticket for £149 per person are available. Travel duration is 3h 59m
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Skyscanner3h 57m009:46Pearson Toronto AirportPearson Toronto Airport12:43Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 09:46:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/04/2026 12:43:00. 50 Economy ticket for £151 per person are available. Travel duration is 3h 57m
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Westjet Airlines3h 59m009:46Pearson Toronto AirportPearson Toronto Airport12:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 09:46:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 12:45:00. 50 Economy ticket for £152 per person are available. Travel duration is 3h 59m
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Skyscanner5h 9m006:10Pearson Toronto AirportPearson Toronto Airport10:19Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 06:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 10:19:00. 50 Economy ticket for £156 per person are available. Travel duration is 5h 9m
Cheapest Buses Sunday
Cheapest Flights Sunday
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 17:35:00. 50 Economy ticket for £54 per person are available. Travel duration is 16h 0m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 28/04/2026 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 12h 50m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 27/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 28/04/2026 11:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 12h 30m
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FlixBus15h 25m002:35Pearson Toronto AirportPearson Toronto Airport17:00Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 27/04/2026 17:00:00. 50 Economy ticket for £63 per person are available. Travel duration is 15h 25m
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Air Canada2h 3m017:20Pearson Toronto AirportPearson Toronto Airport18:23Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 17:20:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 27/04/2026 18:23:00. 50 Economy ticket for £92 per person are available. Travel duration is 2h 3m
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Flair Airlines1h 50m009:25Pearson Toronto AirportPearson Toronto Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £106 per person are available. Travel duration is 1h 50m
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Flair Airlines28h 6m006:30Pearson Toronto AirportPearson Toronto Airport09:36Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 06:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 28/04/2026 09:36:00. 50 Economy ticket for £161 per person are available. Travel duration is 28h 6m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £163 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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Porter Airlines25h 1m009:35Pearson Toronto AirportPearson Toronto Airport09:36Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:35:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 28/04/2026 09:36:00. 50 Economy ticket for £195 per person are available. Travel duration is 25h 1m
Cheapest Buses Monday
Cheapest Flights Monday
What are the fastest trips from Mississauga, ON to Chicago?
You can get to Chicago from Mississauga, ON in just 1h 50m with a Flight from Porter Airlines. But this is just one option, click on any of the offers below to compare it with the other available modes of transportations.
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £93 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m009:25Pearson Toronto AirportPearson Toronto Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £93 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 21/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/04/2026 10:15:00. 50 Economy ticket for £106 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m018:30Pearson Toronto AirportPearson Toronto Airport19:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 18:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 19:25:00. 50 Economy ticket for £116 per person are available. Travel duration is 1h 55m
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Air Canada2h 0m008:10Pearson Toronto AirportPearson Toronto Airport09:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 08:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 09:10:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m007:00Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 07:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 21/04/2026 08:03:00. 50 Economy ticket for £137 per person are available. Travel duration is 2h 3m
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FlixBus19h 50m010:35Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/04/2026 05:25:00. 50 Economy ticket for £47 per person are available. Travel duration is 19h 50m
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FlixBus22h 45m010:35Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/04/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 22/04/2026 08:20:00. 50 Economy ticket for £49 per person are available. Travel duration is 22h 45m
Fastest Flights Tuesday
Fastest Buses Tuesday
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Spirit Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/04/2026 10:15:00. 50 Economy ticket for £229 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/04/2026 10:15:00. 50 Economy ticket for £262 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/04/2026 10:15:00. 50 Economy ticket for £263 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/04/2026 10:15:00. 50 Economy ticket for £310 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m008:15Pearson Toronto AirportPearson Toronto Airport09:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 08:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/04/2026 09:10:00. 50 Economy ticket for £115 per person are available. Travel duration is 1h 55m
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Skyscanner2h 3m011:00Pearson Toronto AirportPearson Toronto Airport12:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/04/2026 12:03:00. 50 Economy ticket for £221 per person are available. Travel duration is 2h 3m
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FlixBus19h 50m002:35Pearson Toronto AirportPearson Toronto Airport21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/04/2026 21:25:00. 50 Economy ticket for £63 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/04/2026 05:25:00. 50 Economy ticket for £63 per person are available. Travel duration is 19h 50m
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FlixBus22h 0m002:35Pearson Toronto AirportPearson Toronto Airport23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 22/04/2026 23:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 22h 0m
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FlixBus22h 45m010:35Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/04/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 23/04/2026 08:20:00. 50 Economy ticket for £77 per person are available. Travel duration is 22h 45m
Fastest Flights Wednesday
Fastest Buses Wednesday
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 10:15:00. 50 Economy ticket for £89 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/04/2026 10:15:00. 50 Economy ticket for £91 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m016:50Pearson Toronto AirportPearson Toronto Airport17:50Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 16:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 17:50:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m007:00Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 07:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 08:03:00. 50 Economy ticket for £157 per person are available. Travel duration is 2h 3m
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Skyscanner2h 10m006:15Pearson Toronto AirportPearson Toronto Airport07:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 06:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 07:25:00. 50 Economy ticket for £143 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m006:15Pearson Toronto AirportPearson Toronto Airport07:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 06:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/04/2026 07:25:00. 50 Economy ticket for £145 per person are available. Travel duration is 2h 10m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 24/04/2026 11:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 12h 50m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 24/04/2026 05:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 17h 40m
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FlixBus20h 35m012:45Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/04/2026 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 24/04/2026 08:20:00. 50 Economy ticket for £73 per person are available. Travel duration is 20h 35m
Fastest Flights Thursday
Fastest Buses Thursday
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CargoLogicAir1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £178 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 15:20:00. 50 Economy ticket for £211 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m012:05Pearson Toronto AirportPearson Toronto Airport13:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/04/2026 13:05:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m011:00Pearson Toronto AirportPearson Toronto Airport12:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/04/2026 12:03:00. 50 Economy ticket for £220 per person are available. Travel duration is 2h 3m
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Skyscanner3h 37m006:10Pearson Toronto AirportPearson Toronto Airport08:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 06:10:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/04/2026 08:47:00. 50 Economy ticket for £229 per person are available. Travel duration is 3h 37m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 24/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 12h 30m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 12h 50m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 40m
Fastest Flights Friday
Fastest Buses Friday
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CargoLogicAir1h 50m011:20Pearson Toronto AirportBilly Bishop Toronto City Airport12:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 25/04/2026 11:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 12:10:00. 50 Economy ticket for £88 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m011:20Pearson Toronto AirportBilly Bishop Toronto City Airport12:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 25/04/2026 11:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 12:10:00. 50 Economy ticket for £91 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m014:15Pearson Toronto AirportPearson Toronto Airport15:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 14:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/04/2026 15:15:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m014:15Pearson Toronto AirportPearson Toronto Airport15:15Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 14:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 15:15:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m017:50Pearson Toronto AirportPearson Toronto Airport18:53Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 17:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 18:53:00. 50 Economy ticket for £116 per person are available. Travel duration is 2h 3m
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United Airlines2h 3m017:50Pearson Toronto AirportPearson Toronto Airport18:53Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 17:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/04/2026 18:53:00. 50 Economy ticket for £118 per person are available. Travel duration is 2h 3m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 25/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 11:25:00. 50 Economy ticket for £68 per person are available. Travel duration is 12h 30m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 11:25:00. 50 Economy ticket for £69 per person are available. Travel duration is 12h 50m
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/04/2026 17:35:00. 50 Economy ticket for £65 per person are available. Travel duration is 16h 0m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 40m
Fastest Flights Saturday
Fastest Buses Saturday
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Porter Airlines1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 26/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/04/2026 15:20:00. 50 Economy ticket for £96 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m014:30Pearson Toronto AirportBilly Bishop Toronto City Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 26/04/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/04/2026 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Spirit Airlines2h 0m008:50Pearson Toronto AirportPearson Toronto Airport09:50Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 08:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 09:50:00. 50 Economy ticket for £115 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m007:00Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 07:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 08:03:00. 50 Economy ticket for £158 per person are available. Travel duration is 2h 3m
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Skyscanner3h 57m009:46Pearson Toronto AirportPearson Toronto Airport12:43Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 09:46:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/04/2026 12:43:00. 50 Economy ticket for £151 per person are available. Travel duration is 3h 57m
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Delta Air Lines3h 59m009:46Pearson Toronto AirportPearson Toronto Airport12:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 09:46:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/04/2026 12:45:00. 50 Economy ticket for £149 per person are available. Travel duration is 3h 59m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 11:25:00. 50 Economy ticket for £76 per person are available. Travel duration is 12h 50m
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FlixBus15h 25m002:35Pearson Toronto AirportPearson Toronto Airport17:00Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 26/04/2026 17:00:00. 50 Economy ticket for £75 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 26/04/2026 17:35:00. 50 Economy ticket for £70 per person are available. Travel duration is 16h 0m
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FlixBus17h 40m012:45Pearson Toronto AirportPearson Toronto Airport05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 05:25:00. 50 Economy ticket for £66 per person are available. Travel duration is 17h 40m
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FlixBus20h 35m012:45Pearson Toronto AirportPearson Toronto Airport08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/04/2026 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 27/04/2026 08:20:00. 50 Economy ticket for £73 per person are available. Travel duration is 20h 35m
Fastest Flights Sunday
Fastest Buses Sunday
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Flair Airlines1h 50m009:25Pearson Toronto AirportPearson Toronto Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £106 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £163 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport10:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 27/04/2026 09:25:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 10:15:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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Air Canada2h 3m017:20Pearson Toronto AirportPearson Toronto Airport18:23Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 17:20:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 27/04/2026 18:23:00. 50 Economy ticket for £92 per person are available. Travel duration is 2h 3m
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Skyscanner3h 37m006:10Pearson Toronto AirportPearson Toronto Airport08:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 06:10:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 08:47:00. 50 Economy ticket for £216 per person are available. Travel duration is 3h 37m
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Westjet Airlines3h 37m006:10Pearson Toronto AirportPearson Toronto Airport08:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 06:10:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 27/04/2026 08:47:00. 50 Economy ticket for £226 per person are available. Travel duration is 3h 37m
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FlixBus12h 30m023:55Mississauga, ONCity Centre Dr / Duke of York Blvd11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 27/04/2026 23:55:00 to Downtown Coach Station, Chicago (USA) arriving at 28/04/2026 11:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 12h 30m
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FlixBus12h 50m023:35Pearson Toronto AirportPearson Toronto Airport11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 28/04/2026 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 12h 50m
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FlixBus15h 25m002:35Pearson Toronto AirportPearson Toronto Airport17:00Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 27/04/2026 17:00:00. 50 Economy ticket for £63 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m002:35Pearson Toronto AirportPearson Toronto Airport17:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 27/04/2026 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 27/04/2026 17:35:00. 50 Economy ticket for £54 per person are available. Travel duration is 16h 0m
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Here you will find all operators and timetables for a
Bus from Mississauga, ON to Chicago
What are the most popular stations in Mississauga, ON and Chicago?
In Mississauga, ON, you will usually depart from City Centre Dr / Duke of York Blvd, Mavis Rd At Cantay Rd Bus Stop or Winston Churchill Coach Station, while in Chicago you will be arriving at California & 35th Street Coach Stop, Downtown Coach Station or 95th Red Line Station, but there are many more stops to explore in both locations.
How do I decide? Some tips and tricks from our experience
Are you having trouble deciding on how to get to Chicago from Mississauga, ON? With 14 connections between 1 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Mississauga, ON and Chicago, you can pay as low as £47 with a Bus from FlixBus.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from Porter Airlines: you will get to Chicago in just 1h 50m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Mississauga, ON and Chicago are FlixBus, Porter Airlines and Skyscanner, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Mississauga, ON and Chicago is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Pearson Toronto Airport or to Cicero, IL, and look at flights from Pearson Toronto Airport, and landing at Chicago Midway Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!Which companies offer a trip from Mississauga, ON to Chicago?
The most popular companies between Mississauga, ON and Chicago, are FlixBus, Porter Airlines and Skyscanner. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Porter Airlines, Skyscanner, CargoLogicAir and 8 more.
All you need to know when you travel from Mississauga, ON to Chicago
Check all information on comfort and services on all modes of transports from Mississauga, ON to Chicago. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Mississauga, ON to Chicago
How can I reach Chicago from Mississauga, ON?
Every day, there are on average 14 connections between Flight and Bus, with which you can get to Chicago from Mississauga, ON.
How far is Chicago from Mississauga, ON?
The distance between Mississauga, ON and Chicago is 679.9 km.
What is the most ecofriendly mode of transport between Mississauga, ON and Chicago?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 18 kgs of CO2, a train 24 kgs, a car 116 kgs, and a flight 167 kgs.
What is the cheapest mode of transport from Mississauga, ON to Chicago?
You can get to Chicago with just £47 by taking a Bus from FlixBus.
What is the fastest way to get from Mississauga, ON to Chicago?
While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Chicago in just 1h 50m with a Flight from Porter Airlines.
More routes to Mississauga, ON and to Chicago
Looking for more options? Here you can see the most popular routes to Mississauga, ON and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
- Trips to Mississauga, ON
- Chicago to Mississauga, ON
- New York to Mississauga, ON
- Trips to Chicago
- Aguascalientes to Chicago
- Atlanta, GA to Chicago
- Bloomington, IN to Chicago
- Cincinnati to Chicago
- Dallas to Chicago
- Durango, DG to Chicago
- El Paso, TX to Chicago
- Houston to Chicago
- Los Angeles to Chicago
- Louisville, KY to Chicago
- Matamoros to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Morelia to Chicago
- Nashville to Chicago
- New York to Chicago
- Nuevo Laredo to Chicago
- Pearson Toronto Airport to Chicago
- Pittsburgh to Chicago
- San Antonio, TX to Chicago
- Santiago de Queretaro to Chicago
- Toronto, ON to Chicago
