What is the best way to travel from Pearson Toronto Airport to Chicago?
Looking for a trip? Compare all the available Buses and Flights for the journey to Chicago from Pearson Toronto Airport. 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 Pearson Toronto Airport?
You can get to Chicago with just $54 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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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 1/20/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/21/2026 5:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 19h 50m
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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 1/20/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/21/2026 8:20:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 22h 45m
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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 1/20/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 10:05:00 AM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 5m
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United Airlines2h 20m05:30 PMPearson Toronto AirportPearson Toronto Airport6:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 5:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 6:50:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 20m
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Porter Airlines2h 0m04:44 PMPearson Toronto AirportPearson Toronto Airport5:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 4:44:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 5:44:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 0m07:04 PMPearson Toronto AirportPearson Toronto Airport8:04 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 7:04:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 8:04:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 0m
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Westjet Airlines3h 46m010:05 AMPearson Toronto AirportPearson Toronto Airport12:51 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 10:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/20/2026 12:51:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 3h 46m
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Westjet Airlines6h 43m012:12 PMPearson Toronto AirportPearson Toronto Airport5:55 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 12:12:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/20/2026 5:55:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 6h 43m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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FlixBus20h 0m010:35 AMPearson Toronto AirportPearson Toronto Airport5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/22/2026 5:35:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 20h 0m
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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 1/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/22/2026 5:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 19h 50m
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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 1/21/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/22/2026 8:20:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 22h 45m
Cheapest Buses Wednesday
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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 1/22/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/23/2026 5:25:00 AM. 50 Economy ticket for $55 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 1/22/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/23/2026 11:25:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 12h 50m
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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 1/22/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/23/2026 8:20:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 20h 35m
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United Airlines2h 6m09:00 AMPearson Toronto AirportPearson Toronto Airport10:06 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 10:06:00 AM. 50 Economy ticket for $137 per person are available. Travel duration is 2h 6m
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United Airlines2h 10m03:30 PMPearson Toronto AirportPearson Toronto Airport4:40 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 3:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 4:40:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 2h 10m
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Flair Airlines28h 25m07:10 AMPearson Toronto AirportPearson Toronto Airport10:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 7:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 10:35:00 AM. 50 Economy ticket for $140 per person are available. Travel duration is 28h 25m
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Flair Airlines13h 31m07:10 AMPearson Toronto AirportPearson Toronto Airport7:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 7:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 7:41:00 PM. 50 Economy ticket for $140 per person are available. Travel duration is 13h 31m
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Westjet Airlines27h 37m05:15 PMPearson Toronto AirportPearson Toronto Airport7:52 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 5:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/23/2026 7:52:00 PM. 50 Economy ticket for $149 per person are available. Travel duration is 27h 37m
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Porter Airlines10h 1m02:15 PMPearson Toronto AirportPearson Toronto Airport11:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 11:16:00 PM. 50 Economy ticket for $149 per person are available. Travel duration is 10h 1m
Cheapest Buses Thursday
Cheapest Flights Thursday
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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 1/23/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/24/2026 11:25:00 AM. 50 Economy ticket for $74 per person are available. Travel duration is 12h 50m
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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 1/23/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/24/2026 5:25:00 AM. 50 Economy ticket for $76 per person are available. Travel duration is 17h 40m
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FlixBus14h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/24/2026 1:25:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 14h 50m
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United Airlines2h 20m05:30 PMPearson Toronto AirportPearson Toronto Airport6:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 5:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 6:50:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 20m
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United Airlines2h 5m09:00 PMPearson Toronto AirportPearson Toronto Airport10:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 9:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 10:05:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 5m
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Porter Airlines2h 15m06:00 AMPearson Toronto AirportPearson Toronto Airport7:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 7:15:00 AM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 15m
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Porter Airlines1h 55m011:35 AMPearson Toronto AirportPearson Toronto Airport12:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 11:35:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 12:30:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 1h 55m
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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 1/23/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/23/2026 8:52:00 AM. 50 Economy ticket for $270 per person are available. Travel duration is 3h 52m
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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 1/23/2026 12:21:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/23/2026 5:29:00 PM. 50 Economy ticket for $270 per person are available. Travel duration is 6h 8m
Cheapest Buses Friday
Cheapest Flights Friday
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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 1/24/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/25/2026 8:20:00 AM. 50 Economy ticket for $75 per person are available. Travel duration is 20h 35m
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FlixBus14h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/25/2026 1:25:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 14h 50m
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FlixBus22h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/24/2026 11:35:00 PM. 50 Economy ticket for $77 per person are available. Travel duration is 22h 0m
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Flair Airlines9h 6m03:40 PMPearson Toronto AirportPearson Toronto Airport11:46 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 3:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/24/2026 11:46:00 PM. 50 Economy ticket for $208 per person are available. Travel duration is 9h 6m
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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 1/24/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 8:52:00 AM. 50 Economy ticket for $271 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 1/24/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 12:46:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 7h 46m
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Westjet Airlines5h 35m06:30 AMPearson Toronto AirportPearson Toronto Airport11:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 6:30:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 11:05:00 AM. 50 Economy ticket for $271 per person are available. Travel duration is 5h 35m
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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 1/24/2026 7:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 12:46:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 6h 1m
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Westjet Airlines16h 37m05:15 PMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 5:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/25/2026 8:52:00 AM. 50 Economy ticket for $271 per person are available. Travel duration is 16h 37m
Cheapest Buses Saturday
Cheapest Flights Saturday
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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 1/25/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/25/2026 9:25:00 PM. 50 Economy ticket for $55 per person are available. Travel duration is 19h 50m
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FlixBus17h 50m012:45 PMPearson Toronto AirportPearson Toronto Airport5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/25/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 5:35:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 17h 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 1/25/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 11:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 12h 50m
Cheapest Buses Sunday
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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 1/26/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 9:25:00 PM. 50 Economy ticket for $54 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 1/26/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/27/2026 11:25:00 AM. 50 Economy ticket for $54 per person are available. Travel duration is 12h 50m
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FlixBus22h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/26/2026 11:35:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 22h 0m
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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 1/26/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 7:38:00 PM. 50 Economy ticket for $193 per person are available. Travel duration is 13h 38m
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Skyscanner2h 15m06:00 AMPearson Toronto AirportPearson Toronto Airport7:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 7:15:00 AM. 50 Economy ticket for $218 per person are available. Travel duration is 2h 15m
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Flair Airlines13h 48m07:10 AMPearson Toronto AirportPearson Toronto Airport7:58 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 7:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/26/2026 7:58:00 PM. 50 Economy ticket for $253 per person are available. Travel duration is 13h 48m
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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 1/26/2026 9:35:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 7:38:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 11h 3m
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Porter Airlines13h 43m07:15 AMPearson Toronto AirportPearson Toronto Airport7:58 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 7:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/26/2026 7:58:00 PM. 50 Economy ticket for $277 per person are available. Travel duration is 13h 43m
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Skyscanner3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/26/2026 8:52:00 AM. 50 Economy ticket for $277 per person are available. Travel duration is 3h 52m
Cheapest Buses Monday
Cheapest Flights Monday
What are the fastest trips from Pearson Toronto Airport to Chicago?
You can get to Chicago from Pearson Toronto Airport in just 1h 55m with a Flight from Porter Airlines. 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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Porter Airlines2h 0m04:44 PMPearson Toronto AirportPearson Toronto Airport5:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 4:44:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 5:44:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 0m07:04 PMPearson Toronto AirportPearson Toronto Airport8:04 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 7:04:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 8:04:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 0m
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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 1/20/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 10:05:00 AM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 5m
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United Airlines2h 20m05:30 PMPearson Toronto AirportPearson Toronto Airport6:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 5:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 6:50:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 20m
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Westjet Airlines3h 46m010:05 AMPearson Toronto AirportPearson Toronto Airport12:51 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 10:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/20/2026 12:51:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 3h 46m
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Westjet Airlines4h 13m010:05 AMPearson Toronto AirportPearson Toronto Airport1:18 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/20/2026 10:05:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/20/2026 1:18:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 4h 13m
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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 1/20/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/21/2026 5:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 19h 50m
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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 1/20/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/21/2026 8:20:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 22h 45m
Fastest Flights Tuesday
Fastest Buses Tuesday
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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 1/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/22/2026 5:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 19h 50m
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FlixBus20h 0m010:35 AMPearson Toronto AirportPearson Toronto Airport5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/22/2026 5:35:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 20h 0m
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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 1/21/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/22/2026 8:20:00 AM. 50 Economy ticket for $58 per person are available. Travel duration is 22h 45m
Fastest Buses Wednesday
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United Airlines2h 6m09:00 AMPearson Toronto AirportPearson Toronto Airport10:06 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 10:06:00 AM. 50 Economy ticket for $137 per person are available. Travel duration is 2h 6m
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United Airlines2h 10m03:30 PMPearson Toronto AirportPearson Toronto Airport4:40 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 3:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 4:40:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 2h 10m
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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 1/22/2026 7:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/22/2026 12:46:00 PM. 50 Economy ticket for $164 per person are available. Travel duration is 6h 1m
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Porter Airlines10h 1m02:15 PMPearson Toronto AirportPearson Toronto Airport11:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 11:16:00 PM. 50 Economy ticket for $149 per person are available. Travel duration is 10h 1m
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Westjet Airlines10h 54m012:25 PMPearson Toronto AirportPearson Toronto Airport10:19 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 12:25:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/22/2026 10:19:00 PM. 50 Economy ticket for $511 per person are available. Travel duration is 10h 54m
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Flair Airlines13h 31m07:10 AMPearson Toronto AirportPearson Toronto Airport7:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/22/2026 7:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/22/2026 7:41:00 PM. 50 Economy ticket for $140 per person are available. Travel duration is 13h 31m
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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 1/22/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/23/2026 11:25:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 12h 50m
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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 1/22/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/23/2026 5:25:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 17h 40m
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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 1/22/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/23/2026 8:20:00 AM. 50 Economy ticket for $59 per person are available. Travel duration is 20h 35m
Fastest Flights Thursday
Fastest Buses Thursday
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Porter Airlines1h 55m011:35 AMPearson Toronto AirportPearson Toronto Airport12:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 11:35:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 12:30:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 1h 55m
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United Airlines2h 5m09:00 PMPearson Toronto AirportPearson Toronto Airport10:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 9:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 10:05:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 5m
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Porter Airlines2h 15m06:00 AMPearson Toronto AirportPearson Toronto Airport7:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 7:15:00 AM. 50 Economy ticket for $215 per person are available. Travel duration is 2h 15m
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United Airlines2h 20m05:30 PMPearson Toronto AirportPearson Toronto Airport6:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 5:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/23/2026 6:50:00 PM. 50 Economy ticket for $199 per person are available. Travel duration is 2h 20m
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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 1/23/2026 10:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/23/2026 12:46:00 PM. 50 Economy ticket for $518 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 1/23/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/23/2026 8:52:00 AM. 50 Economy ticket for $270 per person are available. Travel duration is 3h 52m
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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 1/23/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/24/2026 11:25:00 AM. 50 Economy ticket for $74 per person are available. Travel duration is 12h 50m
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FlixBus14h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/23/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/24/2026 1:25:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 14h 50m
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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 1/23/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/24/2026 5:25:00 AM. 50 Economy ticket for $76 per person are available. Travel duration is 17h 40m
Fastest Flights Friday
Fastest Buses Friday
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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 1/24/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 8:52:00 AM. 50 Economy ticket for $271 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 1/24/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/24/2026 9:41:00 AM. 50 Economy ticket for $271 per person are available. Travel duration is 4h 41m
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Westjet Airlines5h 35m06:30 AMPearson Toronto AirportPearson Toronto Airport11:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 6:30:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 11:05:00 AM. 50 Economy ticket for $271 per person are available. Travel duration is 5h 35m
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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 1/24/2026 7:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 12:46:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 6h 1m
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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 1/24/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/24/2026 12:46:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 7h 46m
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Westjet Airlines8h 8m06:00 AMPearson Toronto AirportPearson Toronto Airport1:08 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/24/2026 1:08:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 8h 8m
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FlixBus14h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/25/2026 1:25:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 14h 50m
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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 1/24/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 1/25/2026 8:20:00 AM. 50 Economy ticket for $75 per person are available. Travel duration is 20h 35m
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FlixBus22h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/24/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/24/2026 11:35:00 PM. 50 Economy ticket for $77 per person are available. Travel duration is 22h 0m
Fastest Flights Saturday
Fastest Buses Saturday
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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 1/25/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 11:25:00 AM. 50 Economy ticket for $57 per person are available. Travel duration is 12h 50m
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FlixBus17h 50m012:45 PMPearson Toronto AirportPearson Toronto Airport5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/25/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 5:35:00 AM. 50 Economy ticket for $55 per person are available. Travel duration is 17h 50m
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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 1/25/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/25/2026 9:25:00 PM. 50 Economy ticket for $55 per person are available. Travel duration is 19h 50m
Fastest Buses Sunday
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Skyscanner2h 15m06:00 AMPearson Toronto AirportPearson Toronto Airport7:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 7:15:00 AM. 50 Economy ticket for $218 per person are available. Travel duration is 2h 15m
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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 1/26/2026 6:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 8:05:00 AM. 50 Economy ticket for $307 per person are available. Travel duration is 2h 15m
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Skyscanner3h 52m06:00 AMPearson Toronto AirportPearson Toronto Airport8:52 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/26/2026 8:52:00 AM. 50 Economy ticket for $277 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 1/26/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 1/26/2026 12:46:00 PM. 50 Economy ticket for $278 per person are available. Travel duration is 7h 46m
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Westjet Airlines9h 40m07:50 AMPearson Toronto AirportPearson Toronto Airport4:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 7:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 4:30:00 PM. 50 Economy ticket for $278 per person are available. Travel duration is 9h 40m
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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 1/26/2026 9:35:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 1/26/2026 7:38:00 PM. 50 Economy ticket for $271 per person are available. Travel duration is 11h 3m
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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 1/26/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 1/27/2026 11:25:00 AM. 50 Economy ticket for $54 per person are available. Travel duration is 12h 50m
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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 1/26/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 1/26/2026 9:25:00 PM. 50 Economy ticket for $54 per person are available. Travel duration is 19h 50m
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FlixBus22h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 1/26/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 1/26/2026 11:35:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 22h 0m
Fastest Flights Monday
Fastest Buses Monday
Here you will find all operators and timetables for a
Bus from Pearson Toronto Airport to Chicago
What are the most popular stations in Pearson Toronto Airport and Chicago?
In Pearson Toronto Airport, you will usually depart from Pearson Toronto Airport or Billy Bishop Toronto City Airport, 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 Pearson Toronto Airport? With 10 connections between 1 Bus and Flight operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Pearson Toronto Airport and Chicago, you can pay as low as $54 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 55m.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 Pearson Toronto Airport 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 Pearson Toronto Airport 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 Mississauga, ON or to Cicero, IL, and look at flights from , 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 Pearson Toronto Airport to Chicago?
The most popular companies between Pearson Toronto Airport 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, United Airlines and 3 more.
All you need to know when you travel from Pearson Toronto Airport to Chicago
Check all information on comfort and services on all modes of transports from Pearson Toronto Airport 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 Pearson Toronto Airport to Chicago
How can I reach Chicago from Pearson Toronto Airport?
Every day, there are on average 10 connections between Bus and Flight, with which you can get to Chicago from Pearson Toronto Airport.
How far is Chicago from Pearson Toronto Airport?
The distance between Pearson Toronto Airport and Chicago is 424.7 miles.
What is the most ecofriendly mode of transport between Pearson Toronto Airport and Chicago?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 18 kgs of CO2, a train 24 kgs, a car 116 kgs, and a flight 168 kgs.
What is the cheapest mode of transport from Pearson Toronto Airport to Chicago?
You can get to Chicago with just $54 by taking a Bus from FlixBus.
What is the fastest way to get from Pearson Toronto Airport 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 55m with a Flight from Porter Airlines.
More routes to Pearson Toronto Airport and to Chicago
Looking for more options? Here you can see the most popular routes to Pearson Toronto Airport and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
- Trips to Pearson Toronto Airport
- Chicago to Pearson Toronto Airport
- Kanata, ON to Pearson Toronto Airport
- London, ON to Pearson Toronto Airport
- Montreal to Pearson Toronto Airport
- Montreal-Trudeau Airport to Pearson Toronto Airport
- Ottawa, ON to Pearson Toronto Airport
- Québec, QC to Pearson Toronto Airport
- Queens Village, NY to Pearson Toronto Airport
- Sault Ste. Marie, ON to Pearson Toronto Airport
- Sudbury, ON to Pearson Toronto Airport
- Windsor, ON to Pearson Toronto Airport
- Winnipeg, MB to Pearson Toronto Airport
- Trips to Chicago
- Aguascalientes to Chicago
- Atlanta, GA to Chicago
- Bloomington, IN to Chicago
- Cincinnati to Chicago
- Dallas to Chicago
- Durango, DG to Chicago
- El Paso, TX to Chicago
- Houston to Chicago
- Laredo, TX to Chicago
- Los Angeles to Chicago
- Louisville, KY to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Monterrey, NL to Chicago
- Nashville to Chicago
- New York to Chicago
- Phoenix, AZ to Chicago
- Pittsburgh to Chicago
- San Antonio, TX to Chicago
- Santiago de Queretaro to Chicago
- St. Louis, MO to Chicago
- Tampa to Chicago
- Toronto, ON to Chicago
