What is the best way to travel from Toronto, ON to Chicago?
Looking for a trip? Check and compare all the available Flights and Buses 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 £42 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 04/02/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 19h 50m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 04/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 17h 0m
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FlixBus16h 10m014:15Toronto, ONFront St West05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 04/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 16h 10m
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United Airlines2h 8m011:00Pearson Toronto AirportPearson Toronto Airport12:08Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 12:08:00. 50 Economy ticket for £89 per person are available. Travel duration is 2h 8m
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United Airlines1h 58m015:30Pearson Toronto AirportPearson Toronto Airport16:28Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 15:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 16:28:00. 50 Economy ticket for £89 per person are available. Travel duration is 1h 58m
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Westjet Airlines6h 43m012:12Pearson Toronto AirportPearson Toronto Airport17:55Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:12:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 04/02/2026 17:55:00. 50 Economy ticket for £124 per person are available. Travel duration is 6h 43m
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Westjet Airlines6h 8m012:21Pearson Toronto AirportPearson Toronto Airport17:29Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:21:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 04/02/2026 17:29:00. 50 Economy ticket for £124 per person are available. Travel duration is 6h 8m
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Westjet Airlines5h 45m012:12Pearson Toronto AirportPearson Toronto Airport16:57Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:12:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 16:57:00. 50 Economy ticket for £124 per person are available. Travel duration is 5h 45m
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Westjet Airlines5h 15m017:15Pearson Toronto AirportPearson Toronto Airport21:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 17:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 21:30:00. 50 Economy ticket for £124 per person are available. Travel duration is 5h 15m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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FlixBus16h 10m014:15Toronto, ONUnion Station Bus Terminal05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 05/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 16h 10m
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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 05/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 17h 40m
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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 05/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 11:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 12h 50m
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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 05/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 21:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 15h 20m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 05/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 17h 0m
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Flair Airlines13h 42m007:10Pearson Toronto AirportPearson Toronto Airport19:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 07:10:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 19:52:00. 50 Economy ticket for £160 per person are available. Travel duration is 13h 42m
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Porter Airlines15h 15m020:20Pearson Toronto AirportPearson Toronto Airport10:35Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 20:20:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 06/02/2026 10:35:00. 50 Economy ticket for £161 per person are available. Travel duration is 15h 15m
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Flair Airlines11h 42m007:10Pearson Toronto AirportPearson Toronto Airport17:52Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 07:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/02/2026 17:52:00. 50 Economy ticket for £169 per person are available. Travel duration is 11h 42m
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Porter Airlines1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 05/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 10:10:00. 50 Economy ticket for £170 per person are available. Travel duration is 1h 50m
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Porter Airlines24h 32m020:20Pearson Toronto AirportPearson Toronto Airport19:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 20:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 19:52:00. 50 Economy ticket for £196 per person are available. Travel duration is 24h 32m
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Air Transat1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 05/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 10:10:00. 50 Economy ticket for £202 per person are available. Travel duration is 1h 50m
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 06/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 11:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 12h 50m
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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 06/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 21:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 15h 20m
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FlixBus14h 25m008:00Toronto, ONUnion Station Bus Terminal21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 06/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 21:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 14h 25m
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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 06/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 11:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 13h 25m
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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 06/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 05:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 17h 40m
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Flair Airlines1h 55m011:35Pearson Toronto AirportPearson Toronto Airport12:30Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 11:35:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 12:30:00. 50 Economy ticket for £145 per person are available. Travel duration is 1h 55m
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Flair Airlines13h 38m007:00Pearson Toronto AirportPearson Toronto Airport19:38Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 07:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 06/02/2026 19:38:00. 50 Economy ticket for £178 per person are available. Travel duration is 13h 38m
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Spirit Airlines26h 18m007:00Pearson Toronto AirportBilly Bishop Toronto City Airport08:18Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 07:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 07/02/2026 08:18:00. 50 Economy ticket for £192 per person are available. Travel duration is 26h 18m
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Porter Airlines11h 3m009:35Pearson Toronto AirportPearson Toronto Airport19:38Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:35:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 06/02/2026 19:38:00. 50 Economy ticket for £195 per person are available. Travel duration is 11h 3m
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CargoLogicAir1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 10:10:00. 50 Economy ticket for £202 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 10:10:00. 50 Economy ticket for £204 per person are available. Travel duration is 1h 50m
Cheapest Buses Friday
Cheapest Flights Friday
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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 07/02/2026 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 14h 5m
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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 07/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 40m
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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 07/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 11:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 12h 50m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 07/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 0m
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FlixBus14h 25m008:00Toronto, ONUnion Station Bus Terminal21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 07/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 21:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 14h 25m
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Flair Airlines9h 7m015:40Pearson Toronto AirportPearson Toronto Airport23:47Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 15:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 23:47:00. 50 Economy ticket for £170 per person are available. Travel duration is 9h 7m
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Porter Airlines14h 17m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport22:42Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 07/02/2026 09:25:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 22:42:00. 50 Economy ticket for £180 per person are available. Travel duration is 14h 17m
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Porter Airlines24h 32m020:20Pearson Toronto AirportPearson Toronto Airport19:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 20:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 19:52:00. 50 Economy ticket for £203 per person are available. Travel duration is 24h 32m
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Westjet Airlines3h 52m006:00Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 07/02/2026 08:52:00. 50 Economy ticket for £206 per person are available. Travel duration is 3h 52m
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Westjet Airlines7h 46m006:00Pearson Toronto AirportPearson Toronto Airport12:46Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 07/02/2026 12:46:00. 50 Economy ticket for £206 per person are available. Travel duration is 7h 46m
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Westjet Airlines4h 41m006:00Pearson Toronto AirportPearson Toronto Airport09:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 09:41:00. 50 Economy ticket for £207 per person are available. Travel duration is 4h 41m
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 08/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 17h 40m
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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 08/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 11:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 12h 50m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 08/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 17h 0m
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FlixBus16h 10m014:15Toronto, ONFront St West05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 08/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 16h 10m
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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 08/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 11:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 13h 25m
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Flair Airlines9h 7m015:40Pearson Toronto AirportPearson Toronto Airport23:47Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 15:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 08/02/2026 23:47:00. 50 Economy ticket for £148 per person are available. Travel duration is 9h 7m
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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 08/02/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 15:20:00. 50 Economy ticket for £154 per person are available. Travel duration is 1h 50m
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Porter Airlines29h 27m018:15Pearson Toronto AirportBilly Bishop Toronto City Airport22:42Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 08/02/2026 18:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 09/02/2026 22:42:00. 50 Economy ticket for £181 per person are available. Travel duration is 29h 27m
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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 08/02/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 15:20:00. 50 Economy ticket for £185 per person are available. Travel duration is 1h 50m
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Westjet Airlines7h 46m006:00Pearson Toronto AirportPearson Toronto Airport12:46Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 12:46:00. 50 Economy ticket for £209 per person are available. Travel duration is 7h 46m
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Westjet Airlines3h 52m006:00Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 08:52:00. 50 Economy ticket for £209 per person are available. Travel duration is 3h 52m
Cheapest Buses Sunday
Cheapest Flights Sunday
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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 09/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 12h 50m
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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 09/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 21:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 15h 20m
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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 09/02/2026 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m008:00Toronto, ONFront St West21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 09/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 21:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 14h 25m
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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 09/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 13h 25m
Cheapest Buses Monday
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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 10/02/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 22h 45m
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FlixBus19h 55m013:25Toronto, ONScarborough Town Center08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 10/02/2026 13:25:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 19h 55m
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FlixBus19h 5m014:15Toronto, ONFront St West08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 10/02/2026 14:15:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 19h 5m
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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 10/02/2026 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £74 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 10/02/2026 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £77 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 10/02/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 13:01:00. 50 Economy ticket for £83 per person are available. Travel duration is 1h 56m
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Skyscanner2h 8m011:00Pearson Toronto AirportPearson Toronto Airport12:08Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 10/02/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 12:08:00. 50 Economy ticket for £83 per person are available. Travel duration is 2h 8m
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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 10/02/2026 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £83 per person are available. Travel duration is 2h 5m
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Delta Air Lines4h 26m006:15Pearson Toronto AirportPearson Toronto Airport09:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 10/02/2026 06:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 09:41:00. 50 Economy ticket for £122 per person are available. Travel duration is 4h 26m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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 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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United Airlines1h 58m015:30Pearson Toronto AirportPearson Toronto Airport16:28Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 15:30:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 16:28:00. 50 Economy ticket for £89 per person are available. Travel duration is 1h 58m
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United Airlines2h 8m011:00Pearson Toronto AirportPearson Toronto Airport12:08Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 12:08:00. 50 Economy ticket for £89 per person are available. Travel duration is 2h 8m
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Westjet Airlines5h 15m017:15Pearson Toronto AirportPearson Toronto Airport21:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 17:15:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 21:30:00. 50 Economy ticket for £124 per person are available. Travel duration is 5h 15m
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Westjet Airlines5h 45m012:12Pearson Toronto AirportPearson Toronto Airport16:57Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:12:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/02/2026 16:57:00. 50 Economy ticket for £124 per person are available. Travel duration is 5h 45m
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Westjet Airlines6h 8m012:21Pearson Toronto AirportPearson Toronto Airport17:29Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:21:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 04/02/2026 17:29:00. 50 Economy ticket for £124 per person are available. Travel duration is 6h 8m
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Westjet Airlines6h 43m012:12Pearson Toronto AirportPearson Toronto Airport17:55Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 04/02/2026 12:12:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 04/02/2026 17:55:00. 50 Economy ticket for £124 per person are available. Travel duration is 6h 43m
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FlixBus16h 10m014:15Toronto, ONFront St West05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 04/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 04/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 17h 0m
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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 04/02/2026 10:35:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 05:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 19h 50m
Fastest Flights Wednesday
Fastest Buses Wednesday
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Porter Airlines1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 05/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 10:10:00. 50 Economy ticket for £170 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 05/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 10:10:00. 50 Economy ticket for £202 per person are available. Travel duration is 1h 50m
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United Airlines2h 15m006:50Pearson Toronto AirportPearson Toronto Airport08:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/02/2026 08:05:00. 50 Economy ticket for £226 per person are available. Travel duration is 2h 15m
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Westjet Airlines3h 52m006:00Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 05/02/2026 08:52:00. 50 Economy ticket for £204 per person are available. Travel duration is 3h 52m
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Westjet Airlines4h 41m006:00Pearson Toronto AirportPearson Toronto Airport09:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/02/2026 09:41:00. 50 Economy ticket for £205 per person are available. Travel duration is 4h 41m
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Flair Airlines11h 42m007:10Pearson Toronto AirportPearson Toronto Airport17:52Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 05/02/2026 07:10:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/02/2026 17:52:00. 50 Economy ticket for £169 per person are available. Travel duration is 11h 42m
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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 05/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 11:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 12h 50m
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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 05/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 05/02/2026 21:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m014:15Toronto, ONUnion Station Bus Terminal05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 05/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 05/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 17h 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 05/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 05:25:00. 50 Economy ticket for £44 per person are available. Travel duration is 17h 40m
Fastest Flights Thursday
Fastest Buses Thursday
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CargoLogicAir1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 10:10:00. 50 Economy ticket for £202 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 10:10:00. 50 Economy ticket for £204 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m009:20Pearson Toronto AirportBilly Bishop Toronto City Airport10:10Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 06/02/2026 09:20:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 10:10:00. 50 Economy ticket for £235 per person are available. Travel duration is 1h 50m
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Flair Airlines1h 55m011:35Pearson Toronto AirportPearson Toronto Airport12:30Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 11:35:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 06/02/2026 12:30:00. 50 Economy ticket for £145 per person are available. Travel duration is 1h 55m
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Skyscanner2h 8m011:00Pearson Toronto AirportPearson Toronto Airport12:08Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 06/02/2026 12:08:00. 50 Economy ticket for £249 per person are available. Travel duration is 2h 8m
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Westjet Airlines5h 49m006:06Pearson Toronto AirportPearson Toronto Airport10:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 06/02/2026 06:06:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 06/02/2026 10:55:00. 50 Economy ticket for £270 per person are available. Travel duration is 5h 49m
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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 06/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 11:25:00. 50 Economy ticket for £42 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 06/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 11:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 13h 25m
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FlixBus14h 25m008:00Toronto, ONUnion Station Bus Terminal21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 06/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 21:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 14h 25m
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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 06/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 06/02/2026 21:25:00. 50 Economy ticket for £42 per person are available. Travel duration is 15h 20m
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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 06/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 05:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 17h 40m
Fastest Flights Friday
Fastest Buses Friday
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United Airlines2h 15m006:50Pearson Toronto AirportPearson Toronto Airport08:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 08:05:00. 50 Economy ticket for £229 per person are available. Travel duration is 2h 15m
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Westjet Airlines3h 52m006:00Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 07/02/2026 08:52:00. 50 Economy ticket for £206 per person are available. Travel duration is 3h 52m
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Westjet Airlines4h 41m006:00Pearson Toronto AirportPearson Toronto Airport09:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 09:41:00. 50 Economy ticket for £207 per person are available. Travel duration is 4h 41m
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Westjet Airlines7h 46m006:00Pearson Toronto AirportPearson Toronto Airport12:46Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 07/02/2026 12:46:00. 50 Economy ticket for £206 per person are available. Travel duration is 7h 46m
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Flair Airlines9h 7m015:40Pearson Toronto AirportPearson Toronto Airport23:47Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 07/02/2026 15:40:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 23:47:00. 50 Economy ticket for £170 per person are available. Travel duration is 9h 7m
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Porter Airlines14h 17m009:25Pearson Toronto AirportBilly Bishop Toronto City Airport22:42Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 07/02/2026 09:25:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 07/02/2026 22:42:00. 50 Economy ticket for £180 per person are available. Travel duration is 14h 17m
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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 07/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 11:25:00. 50 Economy ticket for £65 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 07/02/2026 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 11:25:00. 50 Economy ticket for £64 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m008:00Toronto, ONUnion Station Bus Terminal21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 07/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 07/02/2026 21:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 14h 25m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 07/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 05:25:00. 50 Economy ticket for £65 per person are available. Travel duration is 17h 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 07/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 08/02/2026 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 08/02/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 15:20:00. 50 Economy ticket for £154 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 08/02/2026 14:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 15:20:00. 50 Economy ticket for £185 per person are available. Travel duration is 1h 50m
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United Airlines2h 5m006:50Pearson Toronto AirportPearson Toronto Airport07:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:50:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 08/02/2026 07:55:00. 50 Economy ticket for £231 per person are available. Travel duration is 2h 5m
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Westjet Airlines3h 52m006:00Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 08:52:00. 50 Economy ticket for £209 per person are available. Travel duration is 3h 52m
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Westjet Airlines7h 46m006:00Pearson Toronto AirportPearson Toronto Airport12:46Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:00:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 08/02/2026 12:46:00. 50 Economy ticket for £209 per person are available. Travel duration is 7h 46m
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Westjet Airlines8h 13m006:00Pearson Toronto AirportPearson Toronto Airport13:13Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 08/02/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 08/02/2026 13:13:00. 50 Economy ticket for £209 per person are available. Travel duration is 8h 13m
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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 08/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 11:25:00. 50 Economy ticket for £52 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 08/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 11:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 13h 25m
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FlixBus16h 10m014:15Toronto, ONFront St West05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 08/02/2026 14:15:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m013:25Toronto, ONScarborough Town Center05:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 08/02/2026 13:25:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 17h 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 08/02/2026 12:45:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 05:25:00. 50 Economy ticket for £52 per person are available. Travel duration is 17h 40m
Fastest Flights Sunday
Fastest Buses Sunday
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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 09/02/2026 23:35:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 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 09/02/2026 23:00:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 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 09/02/2026 22:20:00 to Downtown Coach Station, Chicago (USA) arriving at 10/02/2026 11:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m008:00Toronto, ONFront St West21:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 09/02/2026 08:00:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 21:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 14h 25m
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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 09/02/2026 07:05:00 to Downtown Coach Station, Chicago (USA) arriving at 09/02/2026 21:25:00. 50 Economy ticket for £43 per person are available. Travel duration is 15h 20m
Fastest Buses Monday
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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 10/02/2026 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £74 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 10/02/2026 09:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £77 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 10/02/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 13:01:00. 50 Economy ticket for £83 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 10/02/2026 09:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 10:05:00. 50 Economy ticket for £83 per person are available. Travel duration is 2h 5m
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Skyscanner2h 8m011:00Pearson Toronto AirportPearson Toronto Airport12:08Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 10/02/2026 11:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/02/2026 12:08:00. 50 Economy ticket for £83 per person are available. Travel duration is 2h 8m
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Skyscanner3h 37m006:15Pearson Toronto AirportPearson Toronto Airport08:52Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 10/02/2026 06:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/02/2026 08:52:00. 50 Economy ticket for £128 per person are available. Travel duration is 3h 37m
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FlixBus19h 5m014:15Toronto, ONFront St West08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 10/02/2026 14:15:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 19h 5m
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FlixBus19h 55m013:25Toronto, ONScarborough Town Center08:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 10/02/2026 13:25:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 19h 55m
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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 10/02/2026 10:35:00 to 95th Red Line Station, Chicago (USA) arriving at 11/02/2026 08:20:00. 50 Economy ticket for £74 per person are available. Travel duration is 22h 45m
Fastest Flights Tuesday
Fastest Buses Tuesday
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 12 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 Toronto, ON and Chicago, you can pay as low as £42 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 Toronto, ON and Chicago are FlixBus, Westjet Airlines and Porter Airlines, 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, Westjet Airlines and Porter Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Westjet Airlines, Porter Airlines, Flair 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 12 connections between Flight and Bus, 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 £42 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 Porter Airlines.
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
- Ottawa, ON to Toronto, ON
- Québec, QC to Toronto, ON
- Sault Ste. Marie, ON to Toronto, ON
- 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
- Buffalo, NY to Chicago
- Cincinnati to Chicago
- Ciudad Juárez to Chicago
- Dallas to Chicago
- El Paso, TX to Chicago
- Houston to Chicago
- Little Rock, AR to Chicago
- Louisville, KY to Chicago
- Matamoros to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Monterrey, NL to Chicago
- New York to Chicago
- Nuevo Laredo to Chicago
- Oklahoma City, OK to Chicago
- Pearson Toronto Airport to Chicago
- Philadelphia, PA to Chicago
- San Antonio, TX to Chicago
- San Luis Potosí to Chicago
- St. Louis, MO to Chicago
