What is the best way to travel from Toronto, ON to Chicago?
Looking for a trip? Compare all the available Flights and Buses for the journey to Chicago from Toronto, ON. Check between different modes of transportation, look 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 get to Chicago with just $58 by taking a Bus from FlixBus, but you can find many more cheap offers: we have selected the best ones for next few days here for you.
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 12h 50m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/6/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/6/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 15h 20m
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/6/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m08:00 AMToronto, ONUnion Station Bus Terminal9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/6/2026 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/6/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 14h 25m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/6/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 5:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 16h 10m
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Flair Airlines1h 55m011:35 AMPearson Toronto AirportPearson Toronto Airport12:30 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 11:35:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 12:30:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 1h 55m
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Flair Airlines13h 38m07:00 AMPearson Toronto AirportPearson Toronto Airport7:38 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/6/2026 7:38:00 PM. 50 Economy ticket for $244 per person are available. Travel duration is 13h 38m
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Spirit Airlines26h 18m07:00 AMPearson Toronto AirportBilly Bishop Toronto City Airport8:18 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 7:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/7/2026 8:18:00 AM. 50 Economy ticket for $263 per person are available. Travel duration is 26h 18m
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Porter Airlines11h 3m09:35 AMPearson Toronto AirportPearson Toronto Airport7:38 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:35:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/6/2026 7:38:00 PM. 50 Economy ticket for $267 per person are available. Travel duration is 11h 3m
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CargoLogicAir1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 10:10:00 AM. 50 Economy ticket for $277 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 10:10:00 AM. 50 Economy ticket for $278 per person are available. Travel duration is 1h 50m
Cheapest Buses Friday
Cheapest Flights Friday
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/7/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 11:25:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 14h 5m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 5:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 17h 40m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 11:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 12h 50m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/7/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 5:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 17h 0m
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FlixBus14h 25m08:00 AMToronto, ONUnion Station Bus Terminal9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/7/2026 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 9:25:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 14h 25m
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Flair Airlines9h 7m03:40 PMPearson Toronto AirportPearson Toronto Airport11:47 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 3:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 11:47:00 PM. 50 Economy ticket for $232 per person are available. Travel duration is 9h 7m
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Porter Airlines14h 17m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:42 PMChicago 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 2/7/2026 9:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 10:42:00 PM. 50 Economy ticket for $246 per person are available. Travel duration is 14h 17m
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Porter Airlines24h 32m08:20 PMPearson Toronto AirportPearson Toronto Airport7:52 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 8:20:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 7:52:00 PM. 50 Economy ticket for $277 per person are available. Travel duration is 24h 32m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/7/2026 8:52:00 AM. 50 Economy ticket for $282 per person are available. Travel duration is 3h 52m
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Westjet Airlines7h 46m06:00 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/7/2026 12:46:00 PM. 50 Economy ticket for $282 per person are available. Travel duration is 7h 46m
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Westjet Airlines4h 41m06:00 AMPearson Toronto AirportPearson Toronto Airport9:41 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 9:41:00 AM. 50 Economy ticket for $283 per person are available. Travel duration is 4h 41m
Cheapest Buses Saturday
Cheapest Flights Saturday
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 40m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 12h 50m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/8/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 0m
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FlixBus16h 10m02:15 PMToronto, ONFront St West5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/8/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 16h 10m
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FlixBus13h 25m011:00 PMToronto, ONFront St West11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/8/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 13h 25m
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Flair Airlines9h 7m03:40 PMPearson Toronto AirportPearson Toronto Airport11:47 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 3:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/8/2026 11:47:00 PM. 50 Economy ticket for $203 per person are available. Travel duration is 9h 7m
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/8/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 3:20:00 PM. 50 Economy ticket for $211 per person are available. Travel duration is 1h 50m
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Porter Airlines29h 27m06:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport10:42 PMChicago 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 2/8/2026 6:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/9/2026 10:42:00 PM. 50 Economy ticket for $248 per person are available. Travel duration is 29h 27m
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Air Transat1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/8/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 3:20:00 PM. 50 Economy ticket for $254 per person are available. Travel duration is 1h 50m
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Westjet Airlines7h 46m06:00 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 12:46:00 PM. 50 Economy ticket for $285 per person are available. Travel duration is 7h 46m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 8:52:00 AM. 50 Economy ticket for $285 per person are available. Travel duration is 3h 52m
Cheapest Buses Sunday
Cheapest Flights Sunday
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/9/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 15h 20m
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FlixBus13h 25m011:00 PMToronto, ONFront St West11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/9/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 13h 25m
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FlixBus19h 50m02:35 AMPearson Toronto AirportPearson Toronto Airport9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/9/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 9:25:00 PM. 50 Economy ticket for $59 per person are available. Travel duration is 19h 50m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/9/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 12h 50m
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/9/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 14h 5m
Cheapest Buses Monday
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FlixBus22h 45m010:35 AMPearson Toronto AirportPearson Toronto Airport8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 22h 45m
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FlixBus19h 55m01:25 PMToronto, ONScarborough Town Center8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/10/2026 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 19h 55m
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FlixBus19h 5m02:15 PMToronto, ONFront St West8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/10/2026 2:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 19h 5m
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CargoLogicAir1h 50m09:15 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $105 per person are available. Travel duration is 1h 50m
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Air Canada1h 56m012:05 PMPearson Toronto AirportPearson Toronto Airport1:01 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 1:01:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 1h 56m
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Skyscanner2h 8m011:00 AMPearson Toronto AirportPearson Toronto Airport12:08 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 11:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 12:08:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 2h 8m
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United Airlines2h 5m09:00 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 2h 5m
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Delta Air Lines4h 26m06:15 AMPearson Toronto AirportPearson Toronto Airport9:41 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 9:41:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 4h 26m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/11/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $60 per person are available. Travel duration is 16h 10m
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FlixBus19h 50m02:35 AMPearson Toronto AirportPearson Toronto Airport9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/11/2026 9:25:00 PM. 50 Economy ticket for $61 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35 AMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $61 per person are available. Travel duration is 19h 50m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/11/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/11/2026 9:25:00 PM. 50 Economy ticket for $61 per person are available. Travel duration is 15h 20m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/11/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $61 per person are available. Travel duration is 17h 0m
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Porter Airlines16h 7m06:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport9:22 AMChicago 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 2/11/2026 6:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 9:22:00 AM. 50 Economy ticket for $266 per person are available. Travel duration is 16h 7m
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Porter Airlines16h 2m06:20 PMPearson Toronto AirportPearson Toronto Airport9:22 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 6:20:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 9:22:00 AM. 50 Economy ticket for $282 per person are available. Travel duration is 16h 2m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 8:52:00 AM. 50 Economy ticket for $288 per person are available. Travel duration is 3h 52m
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Westjet Airlines3h 41m010:05 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 10:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 12:46:00 PM. 50 Economy ticket for $288 per person are available. Travel duration is 3h 41m
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Westjet Airlines6h 8m012:21 PMPearson Toronto AirportPearson Toronto Airport5:29 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 12:21:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 5:29:00 PM. 50 Economy ticket for $288 per person are available. Travel duration is 6h 8m
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Westjet Airlines20h 50m05:15 PMPearson Toronto AirportPearson Toronto Airport1:05 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 5:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/12/2026 1:05:00 PM. 50 Economy ticket for $288 per person are available. Travel duration is 20h 50m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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FlixBus20h 35m012:45 PMPearson Toronto AirportPearson Toronto Airport8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 20h 35m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/12/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/13/2026 5:25:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 17h 0m
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FlixBus19h 55m01:25 PMToronto, ONScarborough Town Center8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/12/2026 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 19h 55m
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FlixBus19h 5m02:15 PMToronto, ONUnion Station Bus Terminal8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/12/2026 2:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 19h 5m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/12/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/13/2026 5:25:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 10m
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Air Canada1h 55m02:15 PMPearson Toronto AirportPearson Toronto Airport3:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 3:10:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 55m
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Skyscanner1h 58m04:50 PMPearson Toronto AirportPearson Toronto Airport5:48 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 4:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 5:48:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 58m
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United Airlines2h 15m06:45 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 6:45:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 8:00:00 AM. 50 Economy ticket for $124 per person are available. Travel duration is 2h 15m
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CargoLogicAir1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/12/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/12/2026 10:10:00 AM. 50 Economy ticket for $167 per person are available. Travel duration is 1h 50m
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CargoLogicAir6h 0m07:40 PMPearson Toronto AirportBilly Bishop Toronto City Airport12:40 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/12/2026 7:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/13/2026 12:40:00 AM. 50 Economy ticket for $200 per person are available. Travel duration is 6h 0m
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Delta Air Lines6h 59m010:15 AMPearson Toronto AirportPearson Toronto Airport4:14 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 10:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 4:14:00 PM. 50 Economy ticket for $207 per person are available. Travel duration is 6h 59m
Cheapest Buses Thursday
Cheapest Flights Thursday
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. This is not the only option, and you can click on any of the offers below to compare it with the other modes of transportations.
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CargoLogicAir1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 10:10:00 AM. 50 Economy ticket for $277 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 10:10:00 AM. 50 Economy ticket for $278 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/6/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 10:10:00 AM. 50 Economy ticket for $322 per person are available. Travel duration is 1h 50m
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Flair Airlines1h 55m011:35 AMPearson Toronto AirportPearson Toronto Airport12:30 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 11:35:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/6/2026 12:30:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 1h 55m
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Skyscanner2h 8m011:00 AMPearson Toronto AirportPearson Toronto Airport12:08 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 11:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/6/2026 12:08:00 PM. 50 Economy ticket for $341 per person are available. Travel duration is 2h 8m
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Westjet Airlines5h 49m06:06 AMPearson Toronto AirportPearson Toronto Airport10:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 6:06:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/6/2026 10:55:00 AM. 50 Economy ticket for $369 per person are available. Travel duration is 5h 49m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/6/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 12h 50m
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/6/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m08:00 AMToronto, ONUnion Station Bus Terminal9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/6/2026 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/6/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 14h 25m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/6/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/6/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/6/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 5:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 16h 10m
Fastest Flights Friday
Fastest Buses Friday
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United Airlines2h 15m06:50 AMPearson Toronto AirportPearson Toronto Airport8:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 8:05:00 AM. 50 Economy ticket for $312 per person are available. Travel duration is 2h 15m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/7/2026 8:52:00 AM. 50 Economy ticket for $282 per person are available. Travel duration is 3h 52m
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Westjet Airlines4h 41m06:00 AMPearson Toronto AirportPearson Toronto Airport9:41 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 9:41:00 AM. 50 Economy ticket for $283 per person are available. Travel duration is 4h 41m
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Westjet Airlines7h 46m06:00 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/7/2026 12:46:00 PM. 50 Economy ticket for $282 per person are available. Travel duration is 7h 46m
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Flair Airlines9h 7m03:40 PMPearson Toronto AirportPearson Toronto Airport11:47 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 3:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 11:47:00 PM. 50 Economy ticket for $232 per person are available. Travel duration is 9h 7m
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Porter Airlines14h 17m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:42 PMChicago 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 2/7/2026 9:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/7/2026 10:42:00 PM. 50 Economy ticket for $246 per person are available. Travel duration is 14h 17m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 11:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 12h 50m
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/7/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 11:25:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 14h 5m
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FlixBus14h 25m08:00 AMToronto, ONUnion Station Bus Terminal9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/7/2026 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/7/2026 9:25:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 14h 25m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/7/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 5:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 17h 0m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/7/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/8/2026 5:25:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 17h 40m
Fastest Flights Saturday
Fastest Buses Saturday
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/8/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 3:20:00 PM. 50 Economy ticket for $211 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/8/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 3:20:00 PM. 50 Economy ticket for $254 per person are available. Travel duration is 1h 50m
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United Airlines2h 5m06:50 AMPearson Toronto AirportPearson Toronto Airport7:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/8/2026 7:55:00 AM. 50 Economy ticket for $316 per person are available. Travel duration is 2h 5m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 8:52:00 AM. 50 Economy ticket for $285 per person are available. Travel duration is 3h 52m
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Westjet Airlines7h 46m06:00 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/8/2026 12:46:00 PM. 50 Economy ticket for $285 per person are available. Travel duration is 7h 46m
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Westjet Airlines8h 13m06:00 AMPearson Toronto AirportPearson Toronto Airport1:13 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/8/2026 1:13:00 PM. 50 Economy ticket for $285 per person are available. Travel duration is 8h 13m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 12h 50m
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FlixBus13h 25m011:00 PMToronto, ONFront St West11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/8/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 13h 25m
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FlixBus16h 10m02:15 PMToronto, ONFront St West5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/8/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/8/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 0m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/8/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 40m
Fastest Flights Sunday
Fastest Buses Sunday
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/9/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 12h 50m
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FlixBus13h 25m011:00 PMToronto, ONFront St West11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/9/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 13h 25m
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FlixBus14h 5m010:20 PMToronto, ONScarborough Town Center11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/9/2026 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/10/2026 11:25:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 14h 5m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/9/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 9:25:00 PM. 50 Economy ticket for $58 per person are available. Travel duration is 15h 20m
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FlixBus19h 50m02:35 AMPearson Toronto AirportPearson Toronto Airport9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/9/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/9/2026 9:25:00 PM. 50 Economy ticket for $59 per person are available. Travel duration is 19h 50m
Fastest Buses Monday
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CargoLogicAir1h 50m09:15 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $105 per person are available. Travel duration is 1h 50m
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Air Canada1h 56m012:05 PMPearson Toronto AirportPearson Toronto Airport1:01 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 1:01:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 1h 56m
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United Airlines2h 5m09:00 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 10:05:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 2h 5m
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Skyscanner2h 8m011:00 AMPearson Toronto AirportPearson Toronto Airport12:08 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 11:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/10/2026 12:08:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 2h 8m
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Skyscanner3h 37m06:15 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 6:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/10/2026 8:52:00 AM. 50 Economy ticket for $175 per person are available. Travel duration is 3h 37m
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FlixBus19h 5m02:15 PMToronto, ONFront St West8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 2/10/2026 2:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 19h 5m
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FlixBus19h 55m01:25 PMToronto, ONScarborough Town Center8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/10/2026 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 19h 55m
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FlixBus22h 45m010:35 AMPearson Toronto AirportPearson Toronto Airport8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/10/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 2/11/2026 8:20:00 AM. 50 Economy ticket for $101 per person are available. Travel duration is 22h 45m
Fastest Flights Tuesday
Fastest Buses Tuesday
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United Airlines2h 15m06:50 AMPearson Toronto AirportPearson Toronto Airport8:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 6:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/11/2026 8:05:00 AM. 50 Economy ticket for $316 per person are available. Travel duration is 2h 15m
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Westjet Airlines3h 41m010:05 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 10:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 12:46:00 PM. 50 Economy ticket for $288 per person are available. Travel duration is 3h 41m
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Westjet Airlines3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 8:52:00 AM. 50 Economy ticket for $288 per person are available. Travel duration is 3h 52m
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Westjet Airlines6h 1m07:45 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 7:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 12:46:00 PM. 50 Economy ticket for $302 per person are available. Travel duration is 6h 1m
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Westjet Airlines6h 8m012:21 PMPearson Toronto AirportPearson Toronto Airport5:29 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 12:21:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/11/2026 5:29:00 PM. 50 Economy ticket for $288 per person are available. Travel duration is 6h 8m
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Westjet Airlines6h 17m06:30 AMPearson Toronto AirportPearson Toronto Airport11:47 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 6:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/11/2026 11:47:00 AM. 50 Economy ticket for $288 per person are available. Travel duration is 6h 17m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/11/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/11/2026 9:25:00 PM. 50 Economy ticket for $61 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/11/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $60 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/11/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $61 per person are available. Travel duration is 17h 0m
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FlixBus19h 50m02:35 AMPearson Toronto AirportPearson Toronto Airport9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/11/2026 9:25:00 PM. 50 Economy ticket for $61 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35 AMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/11/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 2/12/2026 5:25:00 AM. 50 Economy ticket for $61 per person are available. Travel duration is 19h 50m
Fastest Flights Wednesday
Fastest Buses Wednesday
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CargoLogicAir1h 50m09:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:10 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 2/12/2026 9:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/12/2026 10:10:00 AM. 50 Economy ticket for $167 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m02:15 PMPearson Toronto AirportPearson Toronto Airport3:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 3:10:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 55m
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Skyscanner1h 58m04:50 PMPearson Toronto AirportPearson Toronto Airport5:48 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 4:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 5:48:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 58m
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United Airlines2h 15m06:45 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 6:45:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 2/12/2026 8:00:00 AM. 50 Economy ticket for $124 per person are available. Travel duration is 2h 15m
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Skyscanner3h 44m06:10 AMPearson Toronto AirportPearson Toronto Airport8:54 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/12/2026 8:54:00 AM. 50 Economy ticket for $234 per person are available. Travel duration is 3h 44m
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Westjet Airlines3h 44m06:10 AMPearson Toronto AirportPearson Toronto Airport8:54 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 2/12/2026 8:54:00 AM. 50 Economy ticket for $238 per person are available. Travel duration is 3h 44m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/12/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/13/2026 5:25:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/12/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 2/13/2026 5:25:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 17h 0m
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FlixBus19h 5m02:15 PMToronto, ONUnion Station Bus Terminal8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 2/12/2026 2:15:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 19h 5m
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FlixBus19h 55m01:25 PMToronto, ONScarborough Town Center8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 2/12/2026 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 19h 55m
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FlixBus20h 35m012:45 PMPearson Toronto AirportPearson Toronto Airport8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 2/12/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 2/13/2026 8:20:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 20h 35m
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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 Bus Stop, Downtown Bus 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 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 $58 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, 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 13 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 435.6 miles.
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 $58 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
- Ottawa, ON to Toronto, ON
- Québec, QC to Toronto, ON
- Saskatoon 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 to Chicago
- San Antonio, TX to Chicago
- San Luis Potosí to Chicago
- St. Louis, MO to Chicago
