What is the best way to travel from Toronto, ON to Chicago?
Looking for a trip? Check and compare all the available Buses and Flights to Chicago from Toronto, 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 Toronto, ON?
You can reach Chicago with just £61 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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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 05:35:00. 50 Economy ticket for £79 per person are available. Travel duration is 17h 50m
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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 20/12/2025 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 21/12/2025 08:20:00. 50 Economy ticket for £81 per person are available. Travel duration is 20h 35m
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 20/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 05:35:00. 50 Economy ticket for £94 per person are available. Travel duration is 17h 10m
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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 20/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 20/12/2025 15:20:00. 50 Economy ticket for £238 per person are available. Travel duration is 1h 50m
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Porter Airlines21h 40m012:09Pearson Toronto AirportPearson Toronto Airport08:49Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:09:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 21/12/2025 08:49:00. 50 Economy ticket for £262 per person are available. Travel duration is 21h 40m
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Skyscanner1h 55m011:38Pearson Toronto AirportPearson Toronto Airport12:33Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 11:38:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 12:33:00. 50 Economy ticket for £276 per person are available. Travel duration is 1h 55m
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Skyscanner6h 17m012:09Pearson Toronto AirportPearson Toronto Airport17:26Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:09:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 20/12/2025 17:26:00. 50 Economy ticket for £284 per person are available. Travel duration is 6h 17m
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United Airlines5h 4m019:40Pearson Toronto AirportPearson Toronto Airport23:44Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 19:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 23:44:00. 50 Economy ticket for £299 per person are available. Travel duration is 5h 4m
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Air Canada1h 56m012:05Pearson Toronto AirportPearson Toronto Airport13:01Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 13:01:00. 50 Economy ticket for £319 per person are available. Travel duration is 1h 56m
Cheapest Buses Saturday
Cheapest Flights Saturday
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FlixBus13h 25m023:00Toronto, ONFront St West11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 21/12/2025 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 13h 25m
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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 21/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 21:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 19h 50m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 05:35:00. 50 Economy ticket for £62 per person are available. Travel duration is 17h 50m
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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 21/12/2025 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 11:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 12h 50m
Cheapest Buses Sunday
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 05:35:00. 50 Economy ticket for £80 per person are available. Travel duration is 17h 50m
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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 22/12/2025 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £81 per person are available. Travel duration is 12h 50m
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FlixBus14h 5m022:20Toronto, ONScarborough Town Center11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 22/12/2025 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £82 per person are available. Travel duration is 14h 5m
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FlixBus13h 25m023:00Toronto, ONUnion Station Bus Terminal11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 22/12/2025 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £82 per person are available. Travel duration is 13h 25m
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Porter Airlines1h 50m009:15Pearson Toronto AirportPearson Toronto Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m009:15Pearson Toronto AirportPearson Toronto Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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Allegiant Air4h 0m009:54Pearson Toronto AirportPearson Toronto Airport12:54Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:54:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 12:54:00. 50 Economy ticket for £201 per person are available. Travel duration is 4h 0m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £247 per person are available. Travel duration is 1h 50m
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Westjet Airlines6h 6m006:00Pearson Toronto AirportPearson Toronto Airport11:06Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 11:06:00. 50 Economy ticket for £263 per person are available. Travel duration is 6h 6m
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Westjet Airlines10h 21m006:00Pearson Toronto AirportPearson Toronto Airport15:21Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/12/2025 15:21:00. 50 Economy ticket for £263 per person are available. Travel duration is 10h 21m
Cheapest Buses Monday
Cheapest Flights Monday
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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 23/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 21:25:00. 50 Economy ticket for £98 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 23/12/2025 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 23/12/2025 23:35:00. 50 Economy ticket for £100 per person are available. Travel duration is 22h 0m
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FlixBus25h 55m007:05Toronto, ONScarborough Town Center08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 23/12/2025 07:05:00 to Union Station, Chicago (USA) arriving at 24/12/2025 08:00:00. 50 Economy ticket for £101 per person are available. Travel duration is 25h 55m
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Porter Airlines1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Allegiant Air4h 0m009:54Pearson Toronto AirportPearson Toronto Airport12:54Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 09:54:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 12:54:00. 50 Economy ticket for £202 per person are available. Travel duration is 4h 0m
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United Airlines14h 53m018:00Pearson Toronto AirportPearson Toronto Airport07:53Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 18:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 07:53:00. 50 Economy ticket for £231 per person are available. Travel duration is 14h 53m
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Porter Airlines15h 44m020:30Pearson Toronto AirportPearson Toronto Airport11:14Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 20:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 11:14:00. 50 Economy ticket for £241 per person are available. Travel duration is 15h 44m
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Westjet Airlines4h 0m009:54Pearson Toronto AirportPearson Toronto Airport12:54Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 09:54:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/12/2025 12:54:00. 50 Economy ticket for £262 per person are available. Travel duration is 4h 0m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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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 24/12/2025 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 24/12/2025 23:35:00. 50 Economy ticket for £86 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 24/12/2025 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 25/12/2025 08:20:00. 50 Economy ticket for £92 per person are available. Travel duration is 22h 45m
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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 24/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 24/12/2025 21:25:00. 50 Economy ticket for £92 per person are available. Travel duration is 19h 50m
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FlixBus20h 0m010:35Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/12/2025 05:35:00. 50 Economy ticket for £95 per person are available. Travel duration is 20h 0m
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Porter Airlines1h 50m004:15Pearson Toronto AirportPearson Toronto Airport05:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 04:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/12/2025 05:05:00. 50 Economy ticket for £102 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/12/2025 10:05:00. 50 Economy ticket for £102 per person are available. Travel duration is 1h 50m
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United Airlines5h 4m019:40Pearson Toronto AirportPearson Toronto Airport23:44Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 19:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 23:44:00. 50 Economy ticket for £106 per person are available. Travel duration is 5h 4m
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Skyscanner2h 5m021:00Pearson Toronto AirportPearson Toronto Airport22:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 21:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 22:05:00. 50 Economy ticket for £135 per person are available. Travel duration is 2h 5m
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Delta Air Lines14h 28m006:10Pearson Toronto AirportPearson Toronto Airport19:38Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 06:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 19:38:00. 50 Economy ticket for £145 per person are available. Travel duration is 14h 28m
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Air Canada2h 0m018:30Pearson Toronto AirportPearson Toronto Airport19:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 18:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 19:30:00. 50 Economy ticket for £158 per person are available. Travel duration is 2h 0m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £72 per person are available. Travel duration is 17h 50m
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FlixBus16h 20m014:15Toronto, ONUnion Station Bus Terminal05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 25/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £73 per person are available. Travel duration is 16h 20m
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FlixBus15h 20m007:05Toronto, ONScarborough Town Center21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 25/12/2025 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 25/12/2025 21:25:00. 50 Economy ticket for £74 per person are available. Travel duration is 15h 20m
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 25/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £74 per person are available. Travel duration is 17h 10m
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Air Transat1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/12/2025 15:20:00. 50 Economy ticket for £159 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 25/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/12/2025 15:20:00. 50 Economy ticket for £161 per person are available. Travel duration is 1h 50m
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Skyscanner2h 15m006:00Pearson Toronto AirportPearson Toronto Airport07:15Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 07:15:00. 50 Economy ticket for £196 per person are available. Travel duration is 2h 15m
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Skyscanner2h 13m006:50Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 08:03:00. 50 Economy ticket for £199 per person are available. Travel duration is 2h 13m
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United Airlines2h 5m009:00Pearson Toronto AirportPearson Toronto Airport10:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 10:05:00. 50 Economy ticket for £199 per person are available. Travel duration is 2h 5m
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Air Canada1h 56m012:05Pearson Toronto AirportPearson Toronto Airport13:01Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 13:01:00. 50 Economy ticket for £208 per person are available. Travel duration is 1h 56m
Cheapest Buses Thursday
Cheapest Flights Thursday
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 26/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £76 per person are available. Travel duration is 17h 10m
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FlixBus16h 20m014:15Toronto, ONUnion Station Bus Terminal05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 26/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £76 per person are available. Travel duration is 16h 20m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 17h 50m
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FlixBus16h 20m014:15Toronto, ONFront St West05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 26/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 16h 20m
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Porter Airlines1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/12/2025 15:20:00. 50 Economy ticket for £152 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 26/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/12/2025 10:05:00. 50 Economy ticket for £162 per person are available. Travel duration is 1h 50m
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Skyscanner2h 13m006:50Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 08:03:00. 50 Economy ticket for £200 per person are available. Travel duration is 2h 13m
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United Airlines2h 5m009:00Pearson Toronto AirportPearson Toronto Airport10:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 10:05:00. 50 Economy ticket for £200 per person are available. Travel duration is 2h 5m
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Air Canada2h 0m018:45Pearson Toronto AirportPearson Toronto Airport19:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 18:45:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 19:45:00. 50 Economy ticket for £203 per person are available. Travel duration is 2h 0m
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Westjet Airlines5h 24m017:10Pearson Toronto AirportPearson Toronto Airport21:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 17:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 21:34:00. 50 Economy ticket for £217 per person are available. Travel duration is 5h 24m
Cheapest Buses Friday
Cheapest Flights Friday
What are the fastest trips from Toronto, ON to Chicago?
You can get to Chicago from Toronto, ON in just 1h 50m with a Flight from CargoLogicAir. 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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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 20/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 20/12/2025 15:20:00. 50 Economy ticket for £238 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m011:38Pearson Toronto AirportPearson Toronto Airport12:33Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 11:38:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 12:33:00. 50 Economy ticket for £276 per person are available. Travel duration is 1h 55m
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Air Canada1h 56m012:05Pearson Toronto AirportPearson Toronto Airport13:01Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 13:01:00. 50 Economy ticket for £319 per person are available. Travel duration is 1h 56m
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United Airlines5h 4m019:40Pearson Toronto AirportPearson Toronto Airport23:44Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 19:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 23:44:00. 50 Economy ticket for £299 per person are available. Travel duration is 5h 4m
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Skyscanner6h 17m012:09Pearson Toronto AirportPearson Toronto Airport17:26Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:09:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 20/12/2025 17:26:00. 50 Economy ticket for £284 per person are available. Travel duration is 6h 17m
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CargoLogicAir7h 0m013:20Pearson Toronto AirportBilly Bishop Toronto City Airport19:20Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 20/12/2025 13:20:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 20/12/2025 19:20:00. 50 Economy ticket for £406 per person are available. Travel duration is 7h 0m
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 20/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 05:35:00. 50 Economy ticket for £94 per person are available. Travel duration is 17h 10m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 20/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 05:35:00. 50 Economy ticket for £79 per person are available. Travel duration is 17h 50m
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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 20/12/2025 12:45:00 to 95th Red Line Station, Chicago (USA) arriving at 21/12/2025 08:20:00. 50 Economy ticket for £81 per person are available. Travel duration is 20h 35m
Fastest Flights Saturday
Fastest Buses Saturday
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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 21/12/2025 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 11:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 12h 50m
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FlixBus13h 25m023:00Toronto, ONFront St West11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 21/12/2025 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 13h 25m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 21/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 22/12/2025 05:35:00. 50 Economy ticket for £62 per person are available. Travel duration is 17h 50m
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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 21/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 21/12/2025 21:25:00. 50 Economy ticket for £62 per person are available. Travel duration is 19h 50m
Fastest Buses Sunday
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Porter Airlines1h 50m009:15Pearson Toronto AirportPearson Toronto Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m009:15Pearson Toronto AirportPearson Toronto Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £164 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £247 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 57m013:14Pearson Toronto AirportPearson Toronto Airport14:11Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 13:14:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/12/2025 14:11:00. 50 Economy ticket for £276 per person are available. Travel duration is 1h 57m
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Skyscanner1h 57m013:14Pearson Toronto AirportPearson Toronto Airport14:11Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 13:14:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/12/2025 14:11:00. 50 Economy ticket for £283 per person are available. Travel duration is 1h 57m
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United Airlines2h 5m009:00Pearson Toronto AirportPearson Toronto Airport10:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 22/12/2025 10:05:00. 50 Economy ticket for £290 per person are available. Travel duration is 2h 5m
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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 22/12/2025 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £81 per person are available. Travel duration is 12h 50m
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FlixBus13h 25m023:00Toronto, ONUnion Station Bus Terminal11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 22/12/2025 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £82 per person are available. Travel duration is 13h 25m
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FlixBus14h 5m022:20Toronto, ONScarborough Town Center11:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 22/12/2025 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 11:25:00. 50 Economy ticket for £82 per person are available. Travel duration is 14h 5m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 22/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 05:35:00. 50 Economy ticket for £80 per person are available. Travel duration is 17h 50m
Fastest Flights Monday
Fastest Buses Monday
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Porter Airlines1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 15:20:00. 50 Economy ticket for £177 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 23/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 10:05:00. 50 Economy ticket for £283 per person are available. Travel duration is 1h 50m
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Air Canada1h 56m012:05Pearson Toronto AirportPearson Toronto Airport13:01Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/12/2025 13:01:00. 50 Economy ticket for £291 per person are available. Travel duration is 1h 56m
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Allegiant Air4h 0m009:54Pearson Toronto AirportPearson Toronto Airport12:54Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 09:54:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 23/12/2025 12:54:00. 50 Economy ticket for £202 per person are available. Travel duration is 4h 0m
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Westjet Airlines4h 0m009:54Pearson Toronto AirportPearson Toronto Airport12:54Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 23/12/2025 09:54:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 23/12/2025 12:54:00. 50 Economy ticket for £262 per person are available. Travel duration is 4h 0m
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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 23/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 23/12/2025 21:25:00. 50 Economy ticket for £98 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 23/12/2025 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 23/12/2025 23:35:00. 50 Economy ticket for £100 per person are available. Travel duration is 22h 0m
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FlixBus25h 55m007:05Toronto, ONScarborough Town Center08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 23/12/2025 07:05:00 to Union Station, Chicago (USA) arriving at 24/12/2025 08:00:00. 50 Economy ticket for £101 per person are available. Travel duration is 25h 55m
Fastest Flights Tuesday
Fastest Buses Tuesday
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Porter Airlines1h 50m004:15Pearson Toronto AirportPearson Toronto Airport05:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 04:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/12/2025 05:05:00. 50 Economy ticket for £102 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 24/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/12/2025 10:05:00. 50 Economy ticket for £102 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m018:30Pearson Toronto AirportPearson Toronto Airport19:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 18:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 19:30:00. 50 Economy ticket for £158 per person are available. Travel duration is 2h 0m
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Skyscanner2h 5m021:00Pearson Toronto AirportPearson Toronto Airport22:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 21:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 22:05:00. 50 Economy ticket for £135 per person are available. Travel duration is 2h 5m
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United Airlines5h 4m019:40Pearson Toronto AirportPearson Toronto Airport23:44Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 19:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 24/12/2025 23:44:00. 50 Economy ticket for £106 per person are available. Travel duration is 5h 4m
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Skyscanner6h 6m006:00Pearson Toronto AirportPearson Toronto Airport11:06Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 24/12/2025 11:06:00. 50 Economy ticket for £186 per person are available. Travel duration is 6h 6m
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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 24/12/2025 02:35:00 to Downtown Coach Station, Chicago (USA) arriving at 24/12/2025 21:25:00. 50 Economy ticket for £92 per person are available. Travel duration is 19h 50m
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FlixBus20h 0m010:35Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 24/12/2025 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 25/12/2025 05:35:00. 50 Economy ticket for £95 per person are available. Travel duration is 20h 0m
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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 24/12/2025 02:35:00 to 95th Red Line Station, Chicago (USA) arriving at 24/12/2025 23:35:00. 50 Economy ticket for £86 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 24/12/2025 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 25/12/2025 08:20:00. 50 Economy ticket for £92 per person are available. Travel duration is 22h 45m
Fastest Flights Wednesday
Fastest Buses Wednesday
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Air Transat1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/12/2025 15:20:00. 50 Economy ticket for £159 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 25/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 25/12/2025 15:20:00. 50 Economy ticket for £161 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m014:15Pearson Toronto AirportPearson Toronto Airport15:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 14:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 15:10:00. 50 Economy ticket for £239 per person are available. Travel duration is 1h 55m
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Air Canada1h 56m012:05Pearson Toronto AirportPearson Toronto Airport13:01Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 13:01:00. 50 Economy ticket for £208 per person are available. Travel duration is 1h 56m
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United Airlines2h 5m009:00Pearson Toronto AirportPearson Toronto Airport10:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 10:05:00. 50 Economy ticket for £199 per person are available. Travel duration is 2h 5m
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Skyscanner2h 13m006:50Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 25/12/2025 08:03:00. 50 Economy ticket for £199 per person are available. Travel duration is 2h 13m
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FlixBus15h 20m007:05Toronto, ONScarborough Town Center21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 25/12/2025 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 25/12/2025 21:25:00. 50 Economy ticket for £74 per person are available. Travel duration is 15h 20m
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FlixBus16h 20m014:15Toronto, ONUnion Station Bus Terminal05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 25/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £73 per person are available. Travel duration is 16h 20m
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 25/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £74 per person are available. Travel duration is 17h 10m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 25/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 26/12/2025 05:35:00. 50 Economy ticket for £72 per person are available. Travel duration is 17h 50m
Fastest Flights Thursday
Fastest Buses Thursday
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Porter Airlines1h 50m014:30Pearson Toronto AirportPearson Toronto Airport15:20Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/12/2025 15:20:00. 50 Economy ticket for £152 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m009:15Pearson Toronto AirportBilly Bishop Toronto City Airport10:05Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 26/12/2025 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/12/2025 10:05:00. 50 Economy ticket for £162 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m018:45Pearson Toronto AirportPearson Toronto Airport19:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 18:45:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 19:45:00. 50 Economy ticket for £203 per person are available. Travel duration is 2h 0m
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United Airlines2h 5m009:00Pearson Toronto AirportPearson Toronto Airport10:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 10:05:00. 50 Economy ticket for £200 per person are available. Travel duration is 2h 5m
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Skyscanner2h 13m006:50Pearson Toronto AirportPearson Toronto Airport08:03Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 26/12/2025 08:03:00. 50 Economy ticket for £200 per person are available. Travel duration is 2h 13m
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Westjet Airlines3h 44m006:05Pearson Toronto AirportPearson Toronto Airport08:49Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 06:05:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 26/12/2025 08:49:00. 50 Economy ticket for £473 per person are available. Travel duration is 3h 44m
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FlixBus16h 20m014:15Toronto, ONUnion Station Bus Terminal05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 26/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £76 per person are available. Travel duration is 16h 20m
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FlixBus16h 20m014:15Toronto, ONFront St West05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 26/12/2025 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 16h 20m
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FlixBus17h 10m013:25Toronto, ONScarborough Town Center05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 26/12/2025 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £76 per person are available. Travel duration is 17h 10m
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FlixBus17h 50m012:45Pearson Toronto AirportPearson Toronto Airport05:35ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 26/12/2025 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 27/12/2025 05:35:00. 50 Economy ticket for £77 per person are available. Travel duration is 17h 50m
Fastest Flights Friday
Fastest Buses Friday
Here you will find all operators and timetables for a
Bus from Toronto, ON to Chicago
What are the most popular stations in Toronto, ON and Chicago?
In Toronto, ON, you will usually depart from Front St West, Union Station Bus Terminal or Scarborough Town Center, 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 Toronto, ON? With 13 connections between 1 Bus and Flight 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 Toronto, ON and Chicago, you can pay as low as £61 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 CargoLogicAir: 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 Toronto, ON and Chicago are FlixBus, Skyscanner and CargoLogicAir, 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 Toronto, 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 East York, ON 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 Toronto, ON to Chicago?
The most popular companies between Toronto, ON and Chicago, are FlixBus, Skyscanner and CargoLogicAir. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Skyscanner, CargoLogicAir, Porter Airlines and 7 more.
All you need to know when you travel from Toronto, ON to Chicago
Check all information on comfort and services on all modes of transports from Toronto, 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 Toronto, ON to Chicago
How can I reach Chicago from Toronto, ON?
Every day, there are on average 13 connections between Bus and Flight, with which you can get to Chicago from Toronto, ON.
How far is Chicago from Toronto, ON?
The distance between Toronto, ON and Chicago is 700.9 km.
What is the most ecofriendly mode of transport between Toronto, 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 19 kgs of CO2, a train 25 kgs, a car 119 kgs, and a flight 172 kgs.
What is the cheapest mode of transport from Toronto, ON to Chicago?
You can get to Chicago with just £61 by taking a Bus from FlixBus.
What is the fastest way to get from Toronto, 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 CargoLogicAir.
More routes to Toronto, ON and to Chicago
Looking for more options? Here you can see the most popular routes to Toronto, ON and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
- Trips to Toronto, ON
- Boston, MA to Toronto, ON
- Chicago to Toronto, ON
- Cleveland to Toronto, ON
- Dorval, QC to Toronto, ON
- Edmonton, AB to Toronto, ON
- Halifax, NS to Toronto, ON
- Indianapolis to Toronto, ON
- Moncton, NB to Toronto, ON
- Montreal to Toronto, ON
- New York to Toronto, ON
- Orlando, FL to Toronto, ON
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- Thunder Bay, ON to Toronto, ON
- Washington, DC to Toronto, ON
- Windsor, ON to Toronto, ON
- Winnipeg, MB to Toronto, ON
- Trips to Chicago
- Aguascalientes to Chicago
- Atlanta, GA to Chicago
- Bloomington, IN to Chicago
- Buffalo, NY to Chicago
- Dallas to Chicago
- El Paso, TX to Chicago
- Guadalajara, JC to Chicago
- Houston to Chicago
- Laredo, TX to Chicago
- Little Rock, AR to Chicago
- Louisville, KY to Chicago
- Matamoros to Chicago
- McAllen, TX to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Mississauga, ON to Chicago
- Monterrey, NL to Chicago
- New York to Chicago
- Nuevo Laredo to Chicago
- Pearson Toronto Airport to Chicago
- San Antonio, TX to Chicago
- San Diego to Chicago
- St. Louis, MO to Chicago
