There are 7 ways to get from Toronto to Chicago Loop by plane, train (Amtrak), bus (Flixbus, Greyhound), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Toronto Island Airport to Chicago Midway International Airport
best- Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)YTZ - MDW
2h 34m$121–441Bus
cheapest- Take the bus from Toronto to Detroit Bus StationFlixBus 2701 / ...
- Take the bus from Detroit Bus Station to Chicago Bus StationGreyhound US0160
14h 9m$75–170Train via Detroit
- Take the train from Toronto Union Station to WindsorVIA Rail
- Take the train from Detroit to Chicago Union StationWolverine
10h 38m$82–227Drive 514.2 mi
- Drive from Toronto to Chicago Loop514.2 mi
8h 33m$118–170Fly Toronto Island Airport to Chicago O'Hare International Airport
- Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)YTZ - ORD
2h 39m$186–459Fly Toronto Pearson International Airport to Chicago O'Hare International Airport
- Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)YYZ - ORD
5h 4m$167–455Train
- Take the train from Toronto Union Station to BuffaloVIA Rail
- Take the train from Buffalo Depew Station to Chicago Union StationLake Shore Limited
15h 39m$103–274
Toronto to Chicago Loop by train and car
Questions & Answers
The cheapest way to get from Toronto to Chicago Loop is to bus which costs $75 - $170 and takes 14h 9m.
The fastest way to get from Toronto to Chicago Loop is to fly which takes 2h 34m and costs $120 - $450.
No, there is no direct bus from Toronto to Chicago Loop. However, there are services departing from Toronto and arriving at Washington & Lasalle via Detroit Bus Station and Jefferson & Harrison. The journey, including transfers, takes approximately 14h 9m.
No, there is no direct train from Toronto station to Chicago Loop station. However, there are services departing from Toronto Union Station and arriving at Chicago Union Station via Buffalo Depew Station. The journey, including transfers, takes approximately 15h 39m.
The distance between Toronto and Chicago Loop is 457 miles. The road distance is 517.2 miles.
The best way to get from Toronto to Chicago Loop without a car is to bus which takes 14h 9m and costs $75 - $170.
It takes approximately 2h 34m to get from Toronto to Chicago Loop, including transfers.
Toronto to Chicago Loop bus services, operated by Flixbus USA, depart from Toronto station.
Toronto to Chicago Loop train services, operated by VIA Rail, depart from Toronto Union Station.
The best way to get from Toronto to Chicago Loop is to fly which takes 2h 34m and costs $120 - $450. Alternatively, you can train via Detroit, which costs $80 - $230 and takes 10h 38m, you could also bus, which costs $75 - $170 and takes 14h 9m.
What companies run services between Toronto, ON, Canada and Chicago Loop, IL, USA?
Porter Airlines flies from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a train from Toronto Union Station to Chicago Union Station via Windsor and Detroit in around 10h 38m.
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- Website
- united.com
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Monday to Friday
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 35m
- When
- Monday and Saturday
- Estimated price
- $55–300
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $40–250
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport via Columbus
- Ave. Duration
- 4h 5m
- When
- Sunday
- Estimated price
- $45–270
- Website
- aircanada.com
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Monday to Friday
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 35m
- When
- Monday and Saturday
- Estimated price
- $55–300
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $40–250
- Website
- flyporter.com
Flights from Toronto Island Airport to Chicago Midway International Airport
- Ave. Duration
- 1h 50m
- When
- Every day
- Estimated price
- $110–410
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 2m
- When
- Every day
- Estimated price
- $40–250
- Website
- aa.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 2m
- When
- Every day
- Estimated price
- $40–250
- Phone
- +1 888 842-7245
- Website
- viarail.ca
Train from Toronto Union Station to Windsor
- Ave. Duration
- 4h 18m
- Frequency
- 4 times a day
- Estimated price
- $35–95
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $40–95
- Economy Adult - Advanced Booking
- $40–80
- Economy Escape Advanced Booking - Adult
- $35–50
Train from Toronto Union Station to Buffalo
- Ave. Duration
- 4h 6m
- Frequency
- Once daily
- Estimated price
- $23–85
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $26–85
- Economy Adult - Advanced Booking
- $26–65
- Economy Escape Advanced Booking - Adult
- $23–35
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Detroit to Chicago Union Station
- Ave. Duration
- 5h 6m
- Frequency
- 3 times a day
- Estimated price
- $45–130
- Website
- https://www.amtrak.com/home.html
Train from Buffalo Depew Station to Chicago Union Station
- Ave. Duration
- 10h 33m
- Frequency
- Twice daily
- Estimated price
- $80–190
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Toronto to Detroit Bus Station
- Ave. Duration
- 6h 50m
- Frequency
- 3 times a day
- Estimated price
- $35–70
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 50m
- Frequency
- Twice daily
- Estimated price
- $40–100
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $35–85
- Website
- https://www.greyhound.com/
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More Questions & Answers
Toronto to Chicago Loop bus services, operated by Flixbus USA, arrive at Detroit Bus Station.
Chicago Loop is 1h behind Toronto. It is currently 3:02 AM in Toronto and 2:02 AM in Chicago Loop.
Toronto to Chicago Loop train services, operated by VIA Rail, arrive at Buffalo station.
Yes, the driving distance between Toronto to Chicago Loop is 517 miles. It takes approximately 8h 33m to drive from Toronto to Chicago Loop.
Book your Toronto to Chicago Loop train tickets online with Omio.
There are 1246+ hotels available in Chicago Loop.