There are 9 ways to get from Chicago to Windsor by train (Amtrak), bus (Greyhound, Flixbus), car, plane, bus (Flixbus), train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train (Amtrak)
best- Take the train from Chicago Union Station to DearbornWolverine
5h 35m$67–162Bus
cheapest- Take the bus from Chicago Bus Station to Detroit Bus StationGreyhound US0160
6h 5m$45–110Drive 457.6 km
- Drive from Chicago to Windsor457.6 km
4h 45m$92–132Fly Chicago Midway International Airport to Detroit
- Fly from Chicago Midway International Airport (MDW) to Detroit (DTW)MDW - DTW
4h$77–500Bus via Chicago (Flixbus)
- Take the bus from Chicago to Detroit Bus StationFlixBus 2552
8h 52m$59–137Fly Chicago O'Hare International Airport to Detroit
- Fly from Chicago O'Hare International Airport (ORD) to Detroit (DTW)ORD - DTW
4h 25m$167–500Train to South Bend, fly to Detroit
- Take the train from Van Buren St. to South Bend Airport
- Fly from South Bend (SBN) to Detroit (DTW)SBN - DTW
5h 32m$87–573Fly Chicago O'Hare International Airport to Bishop International Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Bishop International Airport (FNT)ORD - FNT
- Take the bus from Flint to Detroit Bus Station
5h 18m$106–477Train to General Mitchell International Airport, fly to Detroit
- Take the train from Chicago Union Station to Milwaukee
- Fly from General Mitchell International Airport (MKE) to Detroit (DTW)MKE - DTW
5h 35m$277–975
Chicago to Windsor by train and bus (Amtrak)
Questions & Answers
The cheapest way to get from Chicago to Windsor is to bus which costs $45 - $110 and takes 6h 5m.
The fastest way to get from Chicago to Windsor is to fly which takes 4h and costs $75 - $500.
Yes, there is a direct bus departing from Chicago Bus Station station and arriving at Detroit Bus Station station. Services depart four times a day, and operate every day. The journey takes approximately 6h 5m.
The distance between Chicago and Windsor is 450 km. The road distance is 457.6 km.
The best way to get from Chicago to Windsor without a car is to train which takes 5h 35m and costs $65 - $170.
It takes approximately 5h 35m to get from Chicago to Windsor, including transfers.
Chicago to Windsor bus services, operated by Greyhound USA, depart from Chicago Bus Station.
The best way to get from Chicago to Windsor is to train which takes 5h 35m and costs $65 - $170. Alternatively, you can bus, which costs $45 - $110 and takes 6h 5m, you could also fly, which costs $75 - $500 and takes 4h.
Chicago to Windsor bus services, operated by Greyhound USA, arrive at Detroit Bus Station.
Windsor is 1h ahead of Chicago. It is currently 1:10 AM in Chicago and 2:10 AM in Windsor.
What companies run services between Chicago, IL, USA and Windsor, ON, Canada?
Amtrak operates a train from Chicago Union Station to Dearborn 3 times a day. Tickets cost $60–160 and the journey takes 4h 47m. Alternatively, Greyhound USA operates a bus from Chicago Bus Station to Detroit Bus Station 3 times a day. Tickets cost $45–90 and the journey takes 6h 5m. Flixbus USA also services this route twice daily.
- Website
- delta.com
Flights from Chicago Midway International Airport to Detroit
- Ave. Duration
- 1h 15m
- When
- Every day
- Estimated price
- $70–490
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $55–390
Flights from South Bend to Detroit
- Ave. Duration
- 1h 12m
- When
- Every day
- Estimated price
- $65–550
Flights from General Mitchell International Airport to Detroit
- Ave. Duration
- 1h 14m
- When
- Every day
- Estimated price
- $95–700
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 28m
- When
- Every day
- Estimated price
- $55–390
Flights from Chicago O'Hare International Airport to Bishop International Airport
- Ave. Duration
- 1h 19m
- When
- Every day
- Estimated price
- $50–380
- Website
- united.com
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 26m
- When
- Every day
- Estimated price
- $55–390
Flights from Chicago O'Hare International Airport to Bishop International Airport
- Ave. Duration
- 1h 16m
- When
- Every day
- Estimated price
- $50–380
- Website
- southwest.com
Flights from Chicago Midway International Airport to Detroit
- Ave. Duration
- 1h 8m
- When
- Every day
- Estimated price
- $70–490
- Website
- spirit.com
Flights from General Mitchell International Airport to Detroit
- Ave. Duration
- 1h 12m
- When
- Monday and Friday
- Estimated price
- $240–800
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Dearborn
- Ave. Duration
- 4h 47m
- Frequency
- 3 times a day
- Estimated price
- $60–160
- Website
- https://www.amtrak.com/home.html
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $30–55
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
- Ave. Duration
- 1h 58m
- Frequency
- Every 2 hours
- Estimated price
- $18–21
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $18–21
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $45–90
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 7h 55m
- Frequency
- Twice daily
- Estimated price
- $50–110
- Schedules at
- flixbus.com
Bus from Chicago to Detroit Bus Station
- Ave. Duration
- 7h 30m
- Frequency
- Once daily
- Estimated price
- $55–130
- Schedules at
- flixbus.com
- Adult
- $55–130
Bus from Flint to Detroit Bus Station
- Ave. Duration
- 1h 15m
- Frequency
- Once daily
- Estimated price
- $17–40
- Schedules at
- flixbus.com
Want to know more about travelling around Canada
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More Questions & Answers
Yes, the driving distance between Chicago to Windsor is 458 km. It takes approximately 4h 45m to drive from Chicago to Windsor.
Book your Chicago to Windsor bus tickets online with Omio and FlixBus.
There are 396+ hotels available in Windsor.







