What is the best way to travel from Mississauga, ON to Chicago?
Looking for a trip? Compare all the available Flights and Buses for the journey to Chicago from Mississauga, 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 Mississauga, ON?
You can get to Chicago with just $63 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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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/20/2026 5:35:00 PM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 0m
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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 4/20/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/21/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 50m
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/20/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/21/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 30m
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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 4/20/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/20/2026 5:00:00 PM. 50 Economy ticket for $91 per person are available. Travel duration is 15h 25m
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Porter Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 1h 50m
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Spirit Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $153 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 3:15:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 3:15:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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Flair Airlines28h 6m06:30 AMPearson Toronto AirportPearson Toronto Airport9:36 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 6:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:36:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 28h 6m
Cheapest Buses Monday
Cheapest Flights Monday
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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 4/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 5:25:00 AM. 50 Economy ticket for $63 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 4/21/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 8:20:00 AM. 50 Economy ticket for $66 per person are available. Travel duration is 22h 45m
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Porter Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:25 AMPearson Toronto AirportPearson Toronto Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m08:10 AMPearson Toronto AirportPearson Toronto Airport9:10 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 8:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:10:00 AM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Skyscanner1h 55m06:30 PMPearson Toronto AirportPearson Toronto Airport7:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 6:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 7:25:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 1h 55m
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Flair Airlines15h 47m06:30 AMPearson Toronto AirportPearson Toronto Airport9:17 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 6:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:17:00 PM. 50 Economy ticket for $178 per person are available. Travel duration is 15h 47m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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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 4/22/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 9:25:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35 AMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 5:25:00 AM. 50 Economy ticket for $75 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 4/22/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/23/2026 8:20:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 22h 45m
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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 4/22/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 11:35:00 PM. 50 Economy ticket for $84 per person are available. Travel duration is 22h 0m
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/22/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 10:15:00 AM. 50 Economy ticket for $128 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/22/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 10:15:00 AM. 50 Economy ticket for $135 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m08:15 AMPearson Toronto AirportPearson Toronto Airport9:10 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 8:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:10:00 AM. 50 Economy ticket for $155 per person are available. Travel duration is 1h 55m
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Flair Airlines15h 47m06:30 AMPearson Toronto AirportPearson Toronto Airport9:17 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Flair Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:30:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:17:00 PM. 50 Economy ticket for $180 per person are available. Travel duration is 15h 47m
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Skyscanner2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:25:00 AM. 50 Economy ticket for $194 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:25:00 AM. 50 Economy ticket for $196 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 4/23/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/24/2026 5:25:00 AM. 50 Economy ticket for $83 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 4/23/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 8:20:00 AM. 50 Economy ticket for $99 per person are available. Travel duration is 20h 35m
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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 4/23/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/24/2026 11:25:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 12h 50m
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/23/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 10:15:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/23/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 10:15:00 AM. 50 Economy ticket for $123 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m04:50 PMPearson Toronto AirportPearson Toronto Airport5:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 4:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 5:50:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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CargoLogicAir6h 15m07:45 AMPearson Toronto AirportBilly Bishop Toronto City Airport1:00 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/23/2026 7:45:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 1:00:00 PM. 50 Economy ticket for $184 per person are available. Travel duration is 6h 15m
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Skyscanner2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:25:00 AM. 50 Economy ticket for $193 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:25:00 AM. 50 Economy ticket for $196 per person are available. Travel duration is 2h 10m
Cheapest Buses Thursday
Cheapest Flights Thursday
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/24/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 11:25:00 AM. 50 Economy ticket for $86 per person are available. Travel duration is 12h 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 4/24/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 5:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 17h 40m
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FlixBus12h 50m011:35 PMPearson Toronto AirportPearson Toronto Airport11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 50m
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Air Canada2h 0m012:05 PMPearson Toronto AirportPearson Toronto Airport1:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 1:05:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Allegiant Air22h 36m012:00 PMPearson Toronto AirportBilly Bishop Toronto City Airport9:36 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Allegiant Air goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/24/2026 12:00:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 9:36:00 AM. 50 Economy ticket for $213 per person are available. Travel duration is 22h 36m
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Porter Airlines31h 16m010:05 AMPearson Toronto AirportPearson Toronto Airport4:21 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 10:05:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 4:21:00 PM. 50 Economy ticket for $215 per person are available. Travel duration is 31h 16m
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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 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $239 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $240 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $285 per person are available. Travel duration is 1h 50m
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 4/25/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 5:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 17h 40m
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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 5:35:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 16h 0m
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/25/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 11:25:00 AM. 50 Economy ticket for $92 per person are available. Travel duration is 12h 30m
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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 4/25/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 11:25:00 AM. 50 Economy ticket for $93 per person are available. Travel duration is 12h 50m
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CargoLogicAir1h 50m011:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport12:10 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/25/2026 11:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 12:10:00 PM. 50 Economy ticket for $119 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m011:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport12:10 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/25/2026 11:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 12:10:00 PM. 50 Economy ticket for $123 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 3:15:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 3:15:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m05:50 PMPearson Toronto AirportPearson Toronto Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 5:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:53:00 PM. 50 Economy ticket for $157 per person are available. Travel duration is 2h 3m
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United Airlines2h 3m05:50 PMPearson Toronto AirportPearson Toronto Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 5:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:53:00 PM. 50 Economy ticket for $159 per person are available. Travel duration is 2h 3m
Cheapest Buses Saturday
Cheapest Flights Saturday
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/27/2026 5:25:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 17h 40m
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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 5:35:00 PM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 0m
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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 4/26/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $84 per person are available. Travel duration is 20h 35m
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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 4/26/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 5:00:00 PM. 50 Economy ticket for $86 per person are available. Travel duration is 15h 25m
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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 4/26/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/27/2026 11:25:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 12h 50m
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/26/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 3:20:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 1h 50m
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Spirit Airlines2h 0m08:50 AMPearson Toronto AirportPearson Toronto Airport9:50 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 8:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 9:50:00 AM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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Delta Air Lines3h 59m09:46 AMPearson Toronto AirportPearson Toronto Airport12:45 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 4/26/2026 9:46:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 12:45:00 PM. 50 Economy ticket for $201 per person are available. Travel duration is 3h 59m
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Skyscanner3h 57m09:46 AMPearson Toronto AirportPearson Toronto Airport12:43 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 9:46:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 12:43:00 PM. 50 Economy ticket for $203 per person are available. Travel duration is 3h 57m
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Westjet Airlines3h 59m09:46 AMPearson Toronto AirportPearson Toronto Airport12:45 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Westjet Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 9:46:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 12:45:00 PM. 50 Economy ticket for $205 per person are available. Travel duration is 3h 59m
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Skyscanner5h 9m06:10 AMPearson Toronto AirportPearson Toronto Airport10:19 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 6:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 10:19:00 AM. 50 Economy ticket for $210 per person are available. Travel duration is 5h 9m
Cheapest Buses Sunday
Cheapest Flights Sunday
What are the fastest trips from Mississauga, ON to Chicago?
You can get to Chicago from Mississauga, 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 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 1h 50m
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Spirit Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/20/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 10:15:00 AM. 50 Economy ticket for $153 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 3:15:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 3:15:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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Skyscanner7h 33m06:10 AMPearson Toronto AirportPearson Toronto Airport12:43 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 12:43:00 PM. 50 Economy ticket for $200 per person are available. Travel duration is 7h 33m
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/20/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/21/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 30m
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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 4/20/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/21/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 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 4/20/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/20/2026 5:00:00 PM. 50 Economy ticket for $91 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/20/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/20/2026 5:35:00 PM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 0m
Fastest Flights Monday
Fastest Buses Monday
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Porter Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:25 AMPearson Toronto AirportPearson Toronto Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $126 per person are available. Travel duration is 1h 50m
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/21/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $144 per person are available. Travel duration is 1h 50m
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Skyscanner1h 55m06:30 PMPearson Toronto AirportPearson Toronto Airport7:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 6:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 7:25:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 1h 55m
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Air Canada2h 0m08:10 AMPearson Toronto AirportPearson Toronto Airport9:10 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 8:10:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:10:00 AM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m07:00 AMPearson Toronto AirportPearson Toronto Airport8:03 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/21/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 8:03:00 AM. 50 Economy ticket for $185 per person are available. Travel duration is 2h 3m
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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 4/21/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 5:25:00 AM. 50 Economy ticket for $63 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 4/21/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 8:20:00 AM. 50 Economy ticket for $66 per person are available. Travel duration is 22h 45m
Fastest Flights Tuesday
Fastest Buses Tuesday
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/22/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 10:15:00 AM. 50 Economy ticket for $128 per person are available. Travel duration is 1h 50m
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Air Canada1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/22/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 10:15:00 AM. 50 Economy ticket for $135 per person are available. Travel duration is 1h 50m
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Air Canada1h 55m08:15 AMPearson Toronto AirportPearson Toronto Airport9:10 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 8:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:10:00 AM. 50 Economy ticket for $155 per person are available. Travel duration is 1h 55m
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Skyscanner2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:25:00 AM. 50 Economy ticket for $194 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:25:00 AM. 50 Economy ticket for $196 per person are available. Travel duration is 2h 10m
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Skyscanner3h 37m06:10 AMPearson Toronto AirportPearson Toronto Airport8:47 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 8:47:00 AM. 50 Economy ticket for $206 per person are available. Travel duration is 3h 37m
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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 4/22/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 9:25:00 PM. 50 Economy ticket for $75 per person are available. Travel duration is 19h 50m
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FlixBus19h 50m010:35 AMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/22/2026 10:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 5:25:00 AM. 50 Economy ticket for $75 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 4/22/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 11:35:00 PM. 50 Economy ticket for $84 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 4/22/2026 10:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/23/2026 8:20:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 22h 45m
Fastest Flights Wednesday
Fastest Buses Wednesday
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CargoLogicAir1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/23/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 10:15:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m09:25 AMPearson Toronto AirportBilly Bishop Toronto City Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/23/2026 9:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 10:15:00 AM. 50 Economy ticket for $123 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m04:50 PMPearson Toronto AirportPearson Toronto Airport5:50 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 4:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 5:50:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m07:00 AMPearson Toronto AirportPearson Toronto Airport8:03 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 8:03:00 AM. 50 Economy ticket for $212 per person are available. Travel duration is 2h 3m
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Skyscanner2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:25:00 AM. 50 Economy ticket for $193 per person are available. Travel duration is 2h 10m
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Porter Airlines2h 10m06:15 AMPearson Toronto AirportPearson Toronto Airport7:25 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Porter Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 6:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:25:00 AM. 50 Economy ticket for $196 per person are available. Travel duration is 2h 10m
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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 4/23/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/24/2026 11:25:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 12h 50m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/23/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/24/2026 5:25:00 AM. 50 Economy ticket for $83 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 4/23/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 8:20:00 AM. 50 Economy ticket for $99 per person are available. Travel duration is 20h 35m
Fastest Flights Thursday
Fastest Buses Thursday
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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 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $239 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $240 per person are available. Travel duration is 1h 50m
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Air Transat1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Transat goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/24/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 3:20:00 PM. 50 Economy ticket for $285 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m012:05 PMPearson Toronto AirportPearson Toronto Airport1:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 12:05:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 1:05:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m011:00 AMPearson Toronto AirportPearson Toronto Airport12:03 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 11:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 12:03:00 PM. 50 Economy ticket for $297 per person are available. Travel duration is 2h 3m
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Skyscanner3h 37m06:10 AMPearson Toronto AirportPearson Toronto Airport8:47 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 6:10:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 8:47:00 AM. 50 Economy ticket for $310 per person are available. Travel duration is 3h 37m
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/24/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 11:25:00 AM. 50 Economy ticket for $86 per person are available. Travel duration is 12h 30m
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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 4/24/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 11:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 12h 50m
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FlixBus17h 40m012:45 PMPearson Toronto AirportPearson Toronto Airport5:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/24/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 5:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 17h 40m
Fastest Flights Friday
Fastest Buses Friday
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CargoLogicAir1h 50m011:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport12:10 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from CargoLogicAir goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/25/2026 11:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 12:10:00 PM. 50 Economy ticket for $119 per person are available. Travel duration is 1h 50m
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Porter Airlines1h 50m011:20 AMPearson Toronto AirportBilly Bishop Toronto City Airport12:10 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/25/2026 11:20:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 12:10:00 PM. 50 Economy ticket for $123 per person are available. Travel duration is 1h 50m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:15:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 3:15:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Air Canada2h 0m02:15 PMPearson Toronto AirportPearson Toronto Airport3:15 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Air Canada goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 3:15:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 2h 0m
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Skyscanner2h 3m05:50 PMPearson Toronto AirportPearson Toronto Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 5:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:53:00 PM. 50 Economy ticket for $157 per person are available. Travel duration is 2h 3m
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United Airlines2h 3m05:50 PMPearson Toronto AirportPearson Toronto Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 5:50:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:53:00 PM. 50 Economy ticket for $159 per person are available. Travel duration is 2h 3m
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FlixBus12h 30m011:55 PMMississauga, ONCity Centre Dr / Duke of York Blvd11:25 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from City Centre Dr / Duke of York Blvd, Mississauga, ON (Canada) at 4/25/2026 11:55:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 11:25:00 AM. 50 Economy ticket for $92 per person are available. Travel duration is 12h 30m
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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 4/25/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 11:25:00 AM. 50 Economy ticket for $93 per person are available. Travel duration is 12h 50m
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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/25/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/25/2026 5:35:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 16h 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 4/25/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 5:25:00 AM. 50 Economy ticket for $87 per person are available. Travel duration is 17h 40m
Fastest Flights Saturday
Fastest Buses Saturday
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Porter Airlines1h 50m02:30 PMPearson Toronto AirportBilly Bishop Toronto City Airport3:20 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Porter Airlines goes from Billy Bishop Toronto City Airport, Pearson Toronto Airport (Canada) at 4/26/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 3:20:00 PM. 50 Economy ticket for $130 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 4/26/2026 2:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 3:20:00 PM. 50 Economy ticket for $240 per person are available. Travel duration is 1h 50m
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Spirit Airlines2h 0m08:50 AMPearson Toronto AirportPearson Toronto Airport9:50 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 8:50:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 9:50:00 AM. 50 Economy ticket for $156 per person are available. Travel duration is 2h 0m
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United Airlines2h 3m07:00 AMPearson Toronto AirportPearson Toronto Airport8:03 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 8:03:00 AM. 50 Economy ticket for $214 per person are available. Travel duration is 2h 3m
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Skyscanner3h 57m09:46 AMPearson Toronto AirportPearson Toronto Airport12:43 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Skyscanner goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 9:46:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 12:43:00 PM. 50 Economy ticket for $203 per person are available. Travel duration is 3h 57m
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Delta Air Lines3h 59m09:46 AMPearson Toronto AirportPearson Toronto Airport12:45 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 4/26/2026 9:46:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 12:45:00 PM. 50 Economy ticket for $201 per person are available. Travel duration is 3h 59m
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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 4/26/2026 11:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/27/2026 11:25:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 12h 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 4/26/2026 2:35:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 5:00:00 PM. 50 Economy ticket for $86 per person are available. Travel duration is 15h 25m
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FlixBus16h 0m02:35 AMPearson Toronto AirportPearson Toronto Airport5:35 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Pearson Toronto Airport, Pearson Toronto Airport (Canada) at 4/26/2026 2:35:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 5:35:00 PM. 50 Economy ticket for $82 per person are available. Travel duration is 16h 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 4/26/2026 12:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/27/2026 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 4/26/2026 12:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $84 per person are available. Travel duration is 20h 35m
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Here you will find all operators and timetables for a
Bus from Mississauga, ON to Chicago
What are the most popular stations in Mississauga, ON and Chicago?
In Mississauga, ON, you will usually depart from City Centre Dr / Duke of York Blvd, Mavis Rd At Cantay Rd Bus Stop or Winston Churchill Bus Station, 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 Mississauga, 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 Mississauga, ON and Chicago, you can pay as low as $63 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 Mississauga, ON and Chicago are FlixBus, Skyscanner and Porter Airlines, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Mississauga, 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 Pearson Toronto Airport 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 Mississauga, ON to Chicago?
The most popular companies between Mississauga, ON and Chicago, are FlixBus, Skyscanner and Porter Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus
Airlines: Skyscanner, Porter Airlines, Air Canada and 8 more.
All you need to know when you travel from Mississauga, ON to Chicago
Check all information on comfort and services on all modes of transports from Mississauga, 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 Mississauga, ON to Chicago
How can I reach Chicago from Mississauga, ON?
Every day, there are on average 14 connections between Flight and Bus, with which you can get to Chicago from Mississauga, ON.
How far is Chicago from Mississauga, ON?
The distance between Mississauga, ON and Chicago is 422.6 miles.
What is the most ecofriendly mode of transport between Mississauga, 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 18 kgs of CO2, a train 24 kgs, a car 116 kgs, and a flight 167 kgs.
What is the cheapest mode of transport from Mississauga, ON to Chicago?
You can get to Chicago with just $63 by taking a Bus from FlixBus.
What is the fastest way to get from Mississauga, 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 Mississauga, ON and to Chicago
Looking for more options? Here you can see the most popular routes to Mississauga, ON and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
