What is the best way to travel from Toronto, ON to Chicago?
Looking for a trip? Compare all the available Buses and Flights 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 $72 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 12/18/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 11:25:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 12h 50m
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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 12/18/2025 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/19/2025 8:20:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 19h 55m
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FlixBus16h 5m010:20 PMToronto, ONScarborough Town Center1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/18/2025 10:20:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/19/2025 1:25:00 PM. 50 Economy ticket for $72 per person are available. Travel duration is 16h 5m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/18/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 5:35:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 17h 10m
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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 12/18/2025 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 11:25:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 14h 5m
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CargoLogicAir1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/18/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/18/2025 3:20:00 PM. 50 Economy ticket for $103 per person are available. Travel duration is 1h 50m
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United Airlines5h 4m07:40 PMPearson Toronto AirportPearson Toronto Airport11:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/18/2025 7:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 11:44:00 PM. 50 Economy ticket for $140 per person are available. Travel duration is 5h 4m
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Porter Airlines16h 42m01:12 PMPearson Toronto AirportPearson Toronto Airport4:54 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/18/2025 1:12:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/19/2025 4:54:00 AM. 50 Economy ticket for $161 per person are available. Travel duration is 16h 42m
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Delta Air Lines5h 57m03:38 PMPearson Toronto AirportPearson Toronto Airport8:35 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 12/18/2025 3:38:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 8:35:00 PM. 50 Economy ticket for $207 per person are available. Travel duration is 5h 57m
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Delta Air Lines16h 42m06:12 PMPearson Toronto AirportPearson Toronto Airport9:54 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Delta Air Lines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/18/2025 6:12:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/19/2025 9:54:00 AM. 50 Economy ticket for $216 per person are available. Travel duration is 16h 42m
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CargoLogicAir9h 37m01:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport10:07 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/18/2025 1:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 10:07:00 PM. 50 Economy ticket for $231 per person are available. Travel duration is 9h 37m
Cheapest Buses Thursday
Cheapest Flights Thursday
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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 12/19/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $115 per person are available. Travel duration is 17h 50m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/19/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 17h 10m
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FlixBus16h 20m02:15 PMToronto, ONFront St West5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 12/19/2025 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 16h 20m
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FlixBus14h 25m08:00 AMToronto, ONFront St West9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 12/19/2025 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 9:25:00 PM. 50 Economy ticket for $128 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 12/19/2025 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 9:25:00 PM. 50 Economy ticket for $129 per person are available. Travel duration is 15h 20m
Cheapest Buses Friday
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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 12/20/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 5:35:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 17h 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 12/20/2025 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/21/2025 8:20:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 20h 35m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/20/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 5:35:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 17h 10m
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Porter Airlines1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/20/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 10:05:00 AM. 50 Economy ticket for $215 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/20/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 3:20:00 PM. 50 Economy ticket for $319 per person are available. Travel duration is 1h 50m
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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 12/20/2025 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 7:15:00 AM. 50 Economy ticket for $369 per person are available. Travel duration is 2h 15m
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Skyscanner6h 17m012:09 PMPearson Toronto AirportPearson Toronto Airport5:26 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/20/2025 12:09:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 5:26:00 PM. 50 Economy ticket for $380 per person are available. Travel duration is 6h 17m
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Delta Air Lines13h 45m06:10 AMPearson Toronto AirportPearson Toronto Airport6:55 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 12/20/2025 6:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 6:55:00 PM. 50 Economy ticket for $380 per person are available. Travel duration is 13h 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 12/20/2025 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 10:05:00 AM. 50 Economy ticket for $384 per person are available. Travel duration is 2h 5m
Cheapest Buses Saturday
Cheapest Flights Saturday
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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 12/21/2025 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 11:25:00 AM. 50 Economy ticket for $82 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 12/21/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 9:25:00 PM. 50 Economy ticket for $83 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 12/21/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 5:35:00 AM. 50 Economy ticket for $83 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 12/21/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 11:25:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 12h 50m
Cheapest Buses Sunday
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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 12/22/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 5:35:00 AM. 50 Economy ticket for $107 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 12/22/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $109 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 12/22/2025 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $110 per person are available. Travel duration is 14h 5m
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FlixBus13h 25m011:00 PMToronto, ONUnion Station Bus Terminal11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 12/22/2025 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $110 per person are available. Travel duration is 13h 25m
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Porter Airlines1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $220 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 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $220 per person are available. Travel duration is 1h 50m
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Allegiant Air4h 0m09:54 AMPearson Toronto AirportPearson Toronto Airport12:54 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 9:54:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 12:54:00 PM. 50 Economy ticket for $269 per person are available. Travel duration is 4h 0m
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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 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $331 per person are available. Travel duration is 1h 50m
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Westjet Airlines6h 6m06:00 AMPearson Toronto AirportPearson Toronto Airport11:06 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 11:06:00 AM. 50 Economy ticket for $352 per person are available. Travel duration is 6h 6m
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Westjet Airlines10h 21m06:00 AMPearson Toronto AirportPearson Toronto Airport3:21 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/22/2025 3:21:00 PM. 50 Economy ticket for $352 per person are available. Travel duration is 10h 21m
Cheapest Buses Monday
Cheapest Flights Monday
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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 12/23/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 9:25:00 PM. 50 Economy ticket for $132 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 12/23/2025 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/23/2025 11:35:00 PM. 50 Economy ticket for $134 per person are available. Travel duration is 22h 0m
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FlixBus25h 55m07:05 AMToronto, ONScarborough Town Center8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/23/2025 7:05:00 AM to Union Station, Chicago (USA) arriving at 12/24/2025 8:00:00 AM. 50 Economy ticket for $135 per person are available. Travel duration is 25h 55m
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportPearson Toronto Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 3:20:00 PM. 50 Economy ticket for $237 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m02:30 PMPearson Toronto AirportPearson Toronto Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 3:20:00 PM. 50 Economy ticket for $237 per person are available. Travel duration is 1h 50m
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Allegiant Air4h 0m09:54 AMPearson Toronto AirportPearson Toronto Airport12:54 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 9:54:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 12:54:00 PM. 50 Economy ticket for $270 per person are available. Travel duration is 4h 0m
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United Airlines14h 53m06:00 PMPearson Toronto AirportPearson Toronto Airport7:53 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 6:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 7:53:00 AM. 50 Economy ticket for $310 per person are available. Travel duration is 14h 53m
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Porter Airlines15h 44m08:30 PMPearson Toronto AirportPearson Toronto Airport11:14 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 8:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 11:14:00 AM. 50 Economy ticket for $322 per person are available. Travel duration is 15h 44m
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Westjet Airlines4h 0m09:54 AMPearson Toronto AirportPearson Toronto Airport12:54 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 9:54:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/23/2025 12:54:00 PM. 50 Economy ticket for $351 per person are available. Travel duration is 4h 0m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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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 12/24/2025 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:35:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 22h 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 12/24/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/24/2025 9:25:00 PM. 50 Economy ticket for $122 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 12/24/2025 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 8:20:00 AM. 50 Economy ticket for $123 per person are available. Travel duration is 22h 45m
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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 12/24/2025 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/25/2025 5:35:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 20h 0m
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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 12/24/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/24/2025 10:05:00 AM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m04:15 AMPearson Toronto AirportPearson Toronto Airport5:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 4:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/24/2025 5:05:00 AM. 50 Economy ticket for $137 per person are available. Travel duration is 1h 50m
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United Airlines5h 4m07:40 PMPearson Toronto AirportPearson Toronto Airport11:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 7:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 11:44:00 PM. 50 Economy ticket for $141 per person are available. Travel duration is 5h 4m
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Skyscanner2h 5m09:00 PMPearson Toronto AirportPearson Toronto Airport10:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 9:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 10:05:00 PM. 50 Economy ticket for $181 per person are available. Travel duration is 2h 5m
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Delta Air Lines14h 28m06:10 AMPearson Toronto AirportPearson Toronto Airport7:38 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 12/24/2025 6:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 7:38:00 PM. 50 Economy ticket for $194 per person are available. Travel duration is 14h 28m
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Air Canada2h 0m06:30 PMPearson Toronto AirportPearson Toronto Airport7:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 6:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 7:30:00 PM. 50 Economy ticket for $212 per person are available. Travel duration is 2h 0m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/18/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/18/2025 3:20:00 PM. 50 Economy ticket for $103 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 12/18/2025 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 1:01:00 PM. 50 Economy ticket for $269 per person are available. Travel duration is 1h 56m
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Skyscanner2h 5m09:00 PMPearson Toronto AirportPearson Toronto Airport10:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/18/2025 9:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 10:05:00 PM. 50 Economy ticket for $278 per person are available. Travel duration is 2h 5m
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United Airlines5h 4m07:40 PMPearson Toronto AirportPearson Toronto Airport11:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/18/2025 7:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 11:44:00 PM. 50 Economy ticket for $140 per person are available. Travel duration is 5h 4m
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Delta Air Lines5h 57m03:38 PMPearson Toronto AirportPearson Toronto Airport8:35 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 12/18/2025 3:38:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 8:35:00 PM. 50 Economy ticket for $207 per person are available. Travel duration is 5h 57m
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CargoLogicAir9h 37m01:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport10:07 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/18/2025 1:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/18/2025 10:07:00 PM. 50 Economy ticket for $231 per person are available. Travel duration is 9h 37m
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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 12/18/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 11:25:00 AM. 50 Economy ticket for $72 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 12/18/2025 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 11:25:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 14h 5m
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FlixBus16h 5m010:20 PMToronto, ONScarborough Town Center1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/18/2025 10:20:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/19/2025 1:25:00 PM. 50 Economy ticket for $72 per person are available. Travel duration is 16h 5m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/18/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 5:35:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 17h 10m
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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 12/18/2025 1:25:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/19/2025 8:20:00 AM. 50 Economy ticket for $72 per person are available. Travel duration is 19h 55m
Fastest Flights Thursday
Fastest Buses Thursday
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FlixBus14h 25m08:00 AMToronto, ONFront St West9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 12/19/2025 8:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 9:25:00 PM. 50 Economy ticket for $128 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 12/19/2025 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 9:25:00 PM. 50 Economy ticket for $129 per person are available. Travel duration is 15h 20m
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FlixBus16h 20m02:15 PMToronto, ONFront St West5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 12/19/2025 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 16h 20m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/19/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 17h 10m
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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 12/19/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 5:35:00 AM. 50 Economy ticket for $115 per person are available. Travel duration is 17h 50m
Fastest Buses Friday
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Porter Airlines1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/20/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 10:05:00 AM. 50 Economy ticket for $215 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 12/20/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 3:20:00 PM. 50 Economy ticket for $319 per person are available. Travel duration is 1h 50m
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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 12/20/2025 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 10:05:00 AM. 50 Economy ticket for $384 per person are available. Travel duration is 2h 5m
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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 12/20/2025 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 7:15:00 AM. 50 Economy ticket for $369 per person are available. Travel duration is 2h 15m
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Skyscanner6h 17m012:09 PMPearson Toronto AirportPearson Toronto Airport5:26 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/20/2025 12:09:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/20/2025 5:26:00 PM. 50 Economy ticket for $380 per person are available. Travel duration is 6h 17m
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Air Canada8h 35m012:30 AMPearson Toronto AirportPearson Toronto Airport8:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/20/2025 12:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/20/2025 8:05:00 AM. 50 Economy ticket for $418 per person are available. Travel duration is 8h 35m
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FlixBus17h 10m01:25 PMToronto, ONScarborough Town Center5:35 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/20/2025 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 5:35:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 17h 10m
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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 12/20/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 5:35:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 17h 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 12/20/2025 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 12/21/2025 8:20:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 20h 35m
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 12/21/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 11:25:00 AM. 50 Economy ticket for $83 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 12/21/2025 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 11:25:00 AM. 50 Economy ticket for $82 per person are available. Travel duration is 13h 25m
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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 12/21/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 5:35:00 AM. 50 Economy ticket for $83 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 12/21/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 9:25:00 PM. 50 Economy ticket for $83 per person are available. Travel duration is 19h 50m
Fastest Buses Sunday
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Porter Airlines1h 50m09:15 AMPearson Toronto AirportPearson Toronto Airport10:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $220 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 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $220 per person are available. Travel duration is 1h 50m
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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 12/22/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/22/2025 10:05:00 AM. 50 Economy ticket for $331 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 12/22/2025 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/22/2025 1:01:00 PM. 50 Economy ticket for $388 per person are available. Travel duration is 1h 56m
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Porter Airlines1h 57m01:14 PMPearson Toronto AirportPearson Toronto Airport2:11 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 1:14:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/22/2025 2:11:00 PM. 50 Economy ticket for $370 per person are available. Travel duration is 1h 57m
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Skyscanner1h 57m01:14 PMPearson Toronto AirportPearson Toronto Airport2:11 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/22/2025 1:14:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/22/2025 2:11:00 PM. 50 Economy ticket for $379 per person are available. Travel duration is 1h 57m
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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 12/22/2025 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $109 per person are available. Travel duration is 12h 50m
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FlixBus13h 25m011:00 PMToronto, ONUnion Station Bus Terminal11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 12/22/2025 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $110 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 12/22/2025 10:20:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 11:25:00 AM. 50 Economy ticket for $110 per person are available. Travel duration is 14h 5m
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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 12/22/2025 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 5:35:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 17h 50m
Fastest Flights Monday
Fastest Buses Monday
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportPearson Toronto Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 3:20:00 PM. 50 Economy ticket for $237 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m02:30 PMPearson Toronto AirportPearson Toronto Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 3:20:00 PM. 50 Economy ticket for $237 per person are available. Travel duration is 1h 50m
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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 12/23/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 10:05:00 AM. 50 Economy ticket for $378 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 12/23/2025 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/23/2025 1:01:00 PM. 50 Economy ticket for $389 per person are available. Travel duration is 1h 56m
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Allegiant Air4h 0m09:54 AMPearson Toronto AirportPearson Toronto Airport12:54 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 9:54:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/23/2025 12:54:00 PM. 50 Economy ticket for $270 per person are available. Travel duration is 4h 0m
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Westjet Airlines4h 0m09:54 AMPearson Toronto AirportPearson Toronto Airport12:54 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/23/2025 9:54:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/23/2025 12:54:00 PM. 50 Economy ticket for $351 per person are available. Travel duration is 4h 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 12/23/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 9:25:00 PM. 50 Economy ticket for $132 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 12/23/2025 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/23/2025 11:35:00 PM. 50 Economy ticket for $134 per person are available. Travel duration is 22h 0m
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FlixBus25h 55m07:05 AMToronto, ONScarborough Town Center8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 12/23/2025 7:05:00 AM to Union Station, Chicago (USA) arriving at 12/24/2025 8:00:00 AM. 50 Economy ticket for $135 per person are available. Travel duration is 25h 55m
Fastest Flights Tuesday
Fastest Buses Tuesday
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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 12/24/2025 9:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/24/2025 10:05:00 AM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m04:15 AMPearson Toronto AirportPearson Toronto Airport5:05 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 4:15:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/24/2025 5:05:00 AM. 50 Economy ticket for $137 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m06:30 PMPearson Toronto AirportPearson Toronto Airport7:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 6:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 7:30:00 PM. 50 Economy ticket for $212 per person are available. Travel duration is 2h 0m
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Skyscanner2h 5m09:00 PMPearson Toronto AirportPearson Toronto Airport10:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 9:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 10:05:00 PM. 50 Economy ticket for $181 per person are available. Travel duration is 2h 5m
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United Airlines5h 4m07:40 PMPearson Toronto AirportPearson Toronto Airport11:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 7:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 12/24/2025 11:44:00 PM. 50 Economy ticket for $141 per person are available. Travel duration is 5h 4m
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Skyscanner6h 6m06:00 AMPearson Toronto AirportPearson Toronto Airport11:06 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 12/24/2025 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 12/24/2025 11:06:00 AM. 50 Economy ticket for $249 per person are available. Travel duration is 6h 6m
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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 12/24/2025 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/24/2025 9:25:00 PM. 50 Economy ticket for $122 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 12/24/2025 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/25/2025 5:35:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 20h 0m
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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 12/24/2025 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/24/2025 11:35:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 22h 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 12/24/2025 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/25/2025 8:20:00 AM. 50 Economy ticket for $123 per person are available. Travel duration is 22h 45m
Fastest Flights Wednesday
Fastest Buses Wednesday
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 12 connections between 1 Bus and Flight operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Toronto, ON and Chicago, you can pay as low as $72 with a Bus from FlixBus.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from CargoLogicAir: you will get to Chicago in just 1h 50m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Toronto, ON and Chicago are FlixBus, Skyscanner and CargoLogicAir, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Toronto, ON and Chicago is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from East York, ON or to Cicero, IL, and look at flights from Pearson Toronto Airport, and landing at Chicago Midway Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!Which companies offer a trip from Toronto, ON to Chicago?
The most popular companies between Toronto, ON and Chicago, are FlixBus, Skyscanner and CargoLogicAir. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Skyscanner, CargoLogicAir, Porter Airlines and 6 more.
All you need to know when you travel from Toronto, ON to Chicago
Check all information on comfort and services on all modes of transports from Toronto, ON to Chicago. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Toronto, ON to Chicago
How can I reach Chicago from Toronto, ON?
Every day, there are on average 12 connections between Bus and Flight, with which you can get to Chicago from Toronto, ON.
How far is Chicago from Toronto, ON?
The distance between Toronto, ON and Chicago is 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 $72 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
- Bloomington, IN to Chicago
- Ciudad Juárez to Chicago
- Dallas to Chicago
- El Paso, TX to Chicago
- Guadalajara, JC to Chicago
- Houston to Chicago
- Laredo, TX to Chicago
- Little Rock, AR to Chicago
- Louisville, KY to Chicago
- Matamoros to Chicago
- McAllen, TX to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Mississauga, ON to Chicago
- Monterrey, NL to Chicago
- New York to Chicago
- Pearson Toronto Airport to Chicago
- San Antonio, TX to Chicago
- San Diego to Chicago
- St. Louis, MO to Chicago
- Tulsa to Chicago

