What is the best way to travel from Toronto, ON to Chicago?
Looking for a trip? Compare all the available Flights and Buses for the journey to Chicago from Toronto, ON. Check between different modes of transportation, look for the cheapest tickets, fastest rides and most popular stations, and see all 1 available companies to find your perfect trip!
What is the cheapest way to reach Chicago from Toronto, ON?
You can get to Chicago with just $65 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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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 10:00:00 AM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 20m
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FlixBus21h 55m011:10 PMToronto, ONScarborough Town Center8:05 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/2/2026 11:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 8:05:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 21h 55m
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FlixBus15h 20m07:40 PMToronto, ONFront St West10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 10:00:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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FlixBus18h 45m07:40 PMToronto, ONUnion Station Bus Terminal1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/3/2026 1:25:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 18h 45m
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Air Canada2h 0m012:25 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 12:25:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 1:25:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 12m07:20 AMPearson Toronto AirportPearson Toronto Airport8:32 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 7:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 8:32:00 AM. 50 Economy ticket for $278 per person are available. Travel duration is 2h 12m
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Air Canada2h 2m01:15 PMPearson Toronto AirportPearson Toronto Airport2:17 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 1:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/2/2026 2:17:00 PM. 50 Economy ticket for $283 per person are available. Travel duration is 2h 2m
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Skyscanner2h 12m07:20 AMPearson Toronto AirportPearson Toronto Airport8:32 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 7:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 8:32:00 AM. 50 Economy ticket for $286 per person are available. Travel duration is 2h 12m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 8:00:00 AM. 50 Economy ticket for $299 per person are available. Travel duration is 2h 0m
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Flair Airlines30h 54m06:30 AMPearson Toronto AirportPearson Toronto Airport12:24 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 6:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 12:24:00 PM. 50 Economy ticket for $311 per person are available. Travel duration is 30h 54m
Cheapest Buses Tuesday
Cheapest Flights 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 6/3/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/4/2026 5:25:00 AM. 50 Economy ticket for $65 per person are available. Travel duration is 19h 50m
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FlixBus15h 20m07:05 AMToronto, ONScarborough Town Center9:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/3/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 9:25:00 PM. 50 Economy ticket for $65 per person are available. Travel duration is 15h 20m
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FlixBus25h 0m08:00 AMToronto, ONFront St West8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/3/2026 8:00:00 AM to Union Station, Chicago (USA) arriving at 6/4/2026 8:00:00 AM. 50 Economy ticket for $65 per person are available. Travel duration is 25h 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 6/3/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 9:25:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 19h 50m
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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 6/3/2026 7:05:00 AM to Union Station, Chicago (USA) arriving at 6/4/2026 8:00:00 AM. 50 Economy ticket for $66 per person are available. Travel duration is 25h 55m
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Air Canada2h 5m02:45 PMPearson Toronto AirportPearson Toronto Airport3:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 2:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 3:50:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 2h 5m
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Air Canada1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/3/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/3/2026 9:35:00 AM. 50 Economy ticket for $133 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/3/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 1:10:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 55m
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Skyscanner3h 33m06:10 AMPearson Toronto AirportPearson Toronto Airport8:43 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/3/2026 8:43:00 AM. 50 Economy ticket for $228 per person are available. Travel duration is 3h 33m
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Skyscanner2h 2m01:15 PMPearson Toronto AirportPearson Toronto Airport2:17 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 1:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 2:17:00 PM. 50 Economy ticket for $234 per person are available. Travel duration is 2h 2m
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Skyscanner2h 10m03:10 PMPearson Toronto AirportPearson Toronto Airport4:20 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 3:10:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 4:20:00 PM. 50 Economy ticket for $234 per person are available. Travel duration is 2h 10m
Cheapest Buses Wednesday
Cheapest Flights 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 6/4/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 5:25:00 AM. 50 Economy ticket for $80 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 6/4/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/5/2026 8:20:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 20h 35m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/4/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 5:25:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 17h 0m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 7:20:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/4/2026 8:16:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 56m
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Air Canada1h 50m08:45 AMPearson Toronto AirportPearson Toronto Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $189 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/4/2026 1:10:00 PM. 50 Economy ticket for $214 per person are available. Travel duration is 1h 55m
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $217 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $222 per person are available. Travel duration is 1h 50m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/4/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/4/2026 8:00:00 AM. 50 Economy ticket for $224 per person are available. Travel duration is 2h 0m
Cheapest Buses Thursday
Cheapest Flights Thursday
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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 6/5/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 9:25:00 PM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/5/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 16h 10m
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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/5/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 10:00:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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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 6/5/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $78 per person are available. Travel duration is 17h 40m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/5/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $78 per person are available. Travel duration is 17h 0m
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/5/2026 9:35:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/5/2026 9:35:00 AM. 50 Economy ticket for $125 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 9:00:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 2h 0m
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United Airlines5h 30m07:00 PMPearson Toronto AirportPearson Toronto Airport11:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 7:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 11:30:00 PM. 50 Economy ticket for $158 per person are available. Travel duration is 5h 30m
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Skyscanner4h 17m03:35 PMPearson Toronto AirportBilly Bishop Toronto City Airport6:52 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 3:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 6:52:00 PM. 50 Economy ticket for $171 per person are available. Travel duration is 4h 17m
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American Airlines2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from American Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 8:35:00 AM. 50 Economy ticket for $207 per person are available. Travel duration is 2h 10m
Cheapest Buses Friday
Cheapest Flights Friday
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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 6/6/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 40m
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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 6/6/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 9:25:00 PM. 50 Economy ticket for $71 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/6/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 16h 10m
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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/6/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 10:00:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 15h 20m
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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 6/6/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 13h 25m
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Air Canada1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/6/2026 9:35:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 1:10:00 PM. 50 Economy ticket for $134 per person are available. Travel duration is 1h 55m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:20:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/6/2026 8:16:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 56m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:20:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 8:16:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 56m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 8:00:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 5m011:39 AMPearson Toronto AirportPearson Toronto Airport12:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/6/2026 11:39:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 12:44:00 PM. 50 Economy ticket for $198 per person are available. Travel duration is 2h 5m
Cheapest Buses Saturday
Cheapest Flights Saturday
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FlixBus15h 25m02:35 AMPearson Toronto AirportPearson Toronto Airport5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 5:00:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 25m
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FlixBus17h 30m07:05 AMToronto, ONScarborough Town Center11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/7/2026 7:05:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 11:35:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 17h 30m
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FlixBus16h 0m02:00 AMToronto, ONUnion Station Bus Terminal5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/7/2026 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 5:00:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 16h 0m
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FlixBus15h 25m011:00 PMToronto, ONUnion Station Bus Terminal1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/7/2026 11:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 1:25:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 25m
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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 6/7/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 1:25:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 14h 50m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 9:00:00 AM. 50 Economy ticket for $190 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:35:00 AM. 50 Economy ticket for $198 per person are available. Travel duration is 2h 10m
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Skyscanner2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:35:00 AM. 50 Economy ticket for $202 per person are available. Travel duration is 2h 10m
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Skyscanner4h 9m06:05 AMPearson Toronto AirportPearson Toronto Airport9:14 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 6:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/7/2026 9:14:00 AM. 50 Economy ticket for $230 per person are available. Travel duration is 4h 9m
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Skyscanner9h 46m09:45 AMPearson Toronto AirportPearson Toronto Airport6:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 9:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/7/2026 6:31:00 PM. 50 Economy ticket for $230 per person are available. Travel duration is 9h 46m
Cheapest Buses Sunday
Cheapest Flights Sunday
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FlixBus15h 25m02:35 AMPearson Toronto AirportPearson Toronto Airport5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m02:00 AMToronto, ONFront St West5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/8/2026 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 16h 0m
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FlixBus16h 30m01:30 AMToronto, ONScarborough Town Center5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/8/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $67 per person are available. Travel duration is 16h 30m
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FlixBus22h 5m012:45 PMPearson Toronto AirportPearson Toronto Airport9:50 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/9/2026 9:50:00 AM. 50 Economy ticket for $68 per person are available. Travel duration is 22h 5m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/9/2026 5:25:00 AM. 50 Economy ticket for $68 per person are available. Travel duration is 17h 40m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 9:35:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 9:35:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 9:00:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 2h 0m
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CargoLogicAir1h 50m01:45 PMPearson Toronto AirportBilly Bishop Toronto City Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 1:45:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 2:35:00 PM. 50 Economy ticket for $157 per person are available. Travel duration is 1h 50m
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Skyscanner2h 6m010:15 AMPearson Toronto AirportPearson Toronto Airport11:21 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 10:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 11:21:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 6m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 0m
Cheapest Buses Monday
Cheapest Flights Monday
What are the fastest trips from Toronto, ON to Chicago?
You can get to Chicago from Toronto, ON in just 1h 50m with a Flight from Porter Airlines. 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 Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/2/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/2/2026 9:35:00 AM. 50 Economy ticket for $388 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/2/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/2/2026 9:35:00 AM. 50 Economy ticket for $391 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/2/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/2/2026 9:35:00 AM. 50 Economy ticket for $457 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m012:25 PMPearson Toronto AirportPearson Toronto Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 12:25:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 1:25:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 2h 0m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/2/2026 8:00:00 AM. 50 Economy ticket for $299 per person are available. Travel duration is 2h 0m
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Air Canada2h 2m01:15 PMPearson Toronto AirportPearson Toronto Airport2:17 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/2/2026 1:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/2/2026 2:17:00 PM. 50 Economy ticket for $283 per person are available. Travel duration is 2h 2m
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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 10:00:00 AM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 20m
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FlixBus15h 20m07:40 PMToronto, ONFront St West10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 10:00:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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FlixBus18h 45m07:40 PMToronto, ONUnion Station Bus Terminal1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/2/2026 7:40:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/3/2026 1:25:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 18h 45m
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FlixBus21h 55m011:10 PMToronto, ONScarborough Town Center8:05 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/2/2026 11:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 8:05:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 21h 55m
Fastest Flights Tuesday
Fastest Buses Tuesday
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Air Canada1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/3/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/3/2026 9:35:00 AM. 50 Economy ticket for $133 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/3/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/3/2026 9:35:00 AM. 50 Economy ticket for $299 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/3/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 1:10:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 55m
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Skyscanner2h 2m01:15 PMPearson Toronto AirportPearson Toronto Airport2:17 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 1:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 2:17:00 PM. 50 Economy ticket for $234 per person are available. Travel duration is 2h 2m
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Air Canada2h 5m02:45 PMPearson Toronto AirportPearson Toronto Airport3:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 2:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 3:50:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 2h 5m
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Skyscanner2h 10m03:10 PMPearson Toronto AirportPearson Toronto Airport4:20 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/3/2026 3:10:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/3/2026 4:20:00 PM. 50 Economy ticket for $234 per person are available. Travel duration is 2h 10m
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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 6/3/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 9:25:00 PM. 50 Economy ticket for $65 per person are available. Travel duration is 15h 20m
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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 6/3/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/4/2026 5:25:00 AM. 50 Economy ticket for $65 per person are available. Travel duration is 19h 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 6/3/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/3/2026 9:25:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 19h 50m
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FlixBus25h 0m08:00 AMToronto, ONFront St West8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/3/2026 8:00:00 AM to Union Station, Chicago (USA) arriving at 6/4/2026 8:00:00 AM. 50 Economy ticket for $65 per person are available. Travel duration is 25h 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 6/3/2026 7:05:00 AM to Union Station, Chicago (USA) arriving at 6/4/2026 8:00:00 AM. 50 Economy ticket for $66 per person are available. Travel duration is 25h 55m
Fastest Flights Wednesday
Fastest Buses Wednesday
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Air Canada1h 50m08:45 AMPearson Toronto AirportPearson Toronto Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $189 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $217 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $222 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/4/2026 9:35:00 AM. 50 Economy ticket for $261 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/4/2026 1:10:00 PM. 50 Economy ticket for $214 per person are available. Travel duration is 1h 55m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/4/2026 7:20:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/4/2026 8:16:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 56m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/4/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 5:25:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 17h 0m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/4/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 5:25:00 AM. 50 Economy ticket for $80 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 6/4/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/5/2026 8:20:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 20h 35m
Fastest Flights Thursday
Fastest Buses Thursday
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/5/2026 9:35:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/5/2026 9:35:00 AM. 50 Economy ticket for $125 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/5/2026 9:35:00 AM. 50 Economy ticket for $238 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 9:00:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 2h 0m
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American Airlines2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from American Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 8:35:00 AM. 50 Economy ticket for $207 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/5/2026 8:35:00 AM. 50 Economy ticket for $255 per person are available. Travel duration is 2h 10m
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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 6/5/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/5/2026 9:25:00 PM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/5/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 10:00:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/5/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $77 per person are available. Travel duration is 16h 10m
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FlixBus17h 0m01:25 PMToronto, ONScarborough Town Center5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/5/2026 1:25:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $78 per person are available. Travel duration is 17h 0m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/5/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 5:25:00 AM. 50 Economy ticket for $78 per person are available. Travel duration is 17h 40m
Fastest Flights Friday
Fastest Buses Friday
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Air Canada1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/6/2026 9:35:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m012:15 PMPearson Toronto AirportBilly Bishop Toronto City Airport1:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 12:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 1:10:00 PM. 50 Economy ticket for $134 per person are available. Travel duration is 1h 55m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:20:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/6/2026 8:16:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 56m
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Air Canada1h 56m07:20 PMPearson Toronto AirportBilly Bishop Toronto City Airport8:16 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:20:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 8:16:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 1h 56m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/6/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 8:00:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 5m011:39 AMPearson Toronto AirportPearson Toronto Airport12:44 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/6/2026 11:39:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/6/2026 12:44:00 PM. 50 Economy ticket for $198 per person are available. Travel duration is 2h 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 6/6/2026 11:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 13h 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 6/6/2026 7:05:00 AM to Downtown Bus Station, Chicago (USA) arriving at 6/6/2026 9:25:00 PM. 50 Economy ticket for $71 per person are available. Travel duration is 15h 20m
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FlixBus15h 20m07:40 PMToronto, ONUnion Station Bus Terminal10:00 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/6/2026 7:40:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 10:00:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 15h 20m
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FlixBus16h 10m02:15 PMToronto, ONUnion Station Bus Terminal5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/6/2026 2:15:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 16h 10m
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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 6/6/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/7/2026 5:25:00 AM. 50 Economy ticket for $71 per person are available. Travel duration is 17h 40m
Fastest Flights Saturday
Fastest Buses Saturday
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 9:00:00 AM. 50 Economy ticket for $190 per person are available. Travel duration is 2h 0m
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Porter Airlines2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:35:00 AM. 50 Economy ticket for $198 per person are available. Travel duration is 2h 10m
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Skyscanner2h 10m07:25 AMPearson Toronto AirportPearson Toronto Airport8:35 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/7/2026 8:35:00 AM. 50 Economy ticket for $202 per person are available. Travel duration is 2h 10m
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Skyscanner4h 1m09:45 AMPearson Toronto AirportPearson Toronto Airport12:46 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 9:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/7/2026 12:46:00 PM. 50 Economy ticket for $240 per person are available. Travel duration is 4h 1m
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Skyscanner4h 9m06:05 AMPearson Toronto AirportPearson Toronto Airport9:14 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 6:05:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/7/2026 9:14:00 AM. 50 Economy ticket for $230 per person are available. Travel duration is 4h 9m
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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 6/7/2026 11:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 1:25:00 PM. 50 Economy ticket for $76 per person are available. Travel duration is 14h 50m
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FlixBus15h 25m02:35 AMPearson Toronto AirportPearson Toronto Airport5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/7/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 5:00:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 25m
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FlixBus15h 25m011:00 PMToronto, ONUnion Station Bus Terminal1:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/7/2026 11:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 1:25:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m02:00 AMToronto, ONUnion Station Bus Terminal5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Union Station Bus Terminal, Toronto, ON (Canada) at 6/7/2026 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 5:00:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 16h 0m
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FlixBus17h 30m07:05 AMToronto, ONScarborough Town Center11:35 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/7/2026 7:05:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/7/2026 11:35:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 17h 30m
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CargoLogicAir1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 9:35:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m08:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport9:35 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 9:35:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m01:45 PMPearson Toronto AirportBilly Bishop Toronto City Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 6/8/2026 1:45:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 6/8/2026 2:35:00 PM. 50 Economy ticket for $157 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m08:00 AMPearson Toronto AirportPearson Toronto Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 8:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 9:00:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 2h 0m
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United Airlines2h 0m07:00 AMPearson Toronto AirportPearson Toronto Airport8:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 0m
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Skyscanner2h 6m010:15 AMPearson Toronto AirportPearson Toronto Airport11:21 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 10:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 6/8/2026 11:21:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 2h 6m
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FlixBus15h 25m02:35 AMPearson Toronto AirportPearson Toronto Airport5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m02:00 AMToronto, ONFront St West5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Front St West, Toronto, ON (Canada) at 6/8/2026 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $66 per person are available. Travel duration is 16h 0m
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FlixBus16h 30m01:30 AMToronto, ONScarborough Town Center5:00 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Scarborough Town Center, Toronto, ON (Canada) at 6/8/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 6/8/2026 5:00:00 PM. 50 Economy ticket for $67 per person are available. Travel duration is 16h 30m
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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 6/8/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 6/9/2026 5:25:00 AM. 50 Economy ticket for $68 per person are available. Travel duration is 17h 40m
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FlixBus22h 5m012:45 PMPearson Toronto AirportPearson Toronto Airport9:50 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 6/8/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 6/9/2026 9:50:00 AM. 50 Economy ticket for $68 per person are available. Travel duration is 22h 5m
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Here you will find all operators and timetables for a
Bus from Toronto, ON to Chicago
What are the most popular stations in Toronto, ON and Chicago?
In Toronto, ON, you will usually depart from Front St West, Union Station Bus Terminal or Scarborough Town Center, while in Chicago you will be arriving at California & 35th Street Bus Stop, Downtown Bus Station or 95th Red Line Station, but there are many more stops to explore in both locations.
How do I decide? Some tips and tricks from our experience
Are you having trouble deciding on how to get to Chicago from Toronto, ON? With 14 connections between 1 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Toronto, ON and Chicago, you can pay as low as $65 with a Bus from FlixBus.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from Porter Airlines: you will get to Chicago in just 1h 50m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Toronto, ON and Chicago are FlixBus, Skyscanner and Air Canada, 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 Air Canada. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Skyscanner, Air Canada, Porter Airlines and 8 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 14 connections between Flight and Bus, with which you can get to Chicago from Toronto, ON.
How far is Chicago from Toronto, ON?
The distance between Toronto, ON and Chicago is 435.6 miles.
What is the most ecofriendly mode of transport between Toronto, ON and Chicago?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 19 kgs of CO2, a train 25 kgs, a car 119 kgs, and a flight 172 kgs.
What is the cheapest mode of transport from Toronto, ON to Chicago?
You can get to Chicago with just $65 by taking a Bus from FlixBus.
What is the fastest way to get from Toronto, ON to Chicago?
While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Chicago in just 1h 50m with a Flight from Porter Airlines.
More routes to Toronto, ON and to Chicago
Looking for more options? Here you can see the most popular routes to Toronto, ON and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
