There are 7 ways to get from Windsor to Chicago by bus (Greyhound, Flixbus), train (Amtrak), car, plane, bus (Flixbus), 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.
Bus
best- Take the bus from Detroit Bus Station to Chicago Bus StationGreyhound US0160
6h 5m$35–110Train (Amtrak)
- Take the train from Detroit to Chicago Union StationWolverine
6h 20m$47–132Drive 284.4 mi
- Drive from Windsor to Chicago284.4 mi
4h 43m$66–94Fly Detroit to Chicago Midway International Airport
- Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)DTW - MDW
3h 48m$49–317Bus via Chicago (Flixbus)
- Take the bus from Detroit Bus Station to ChicagoFlixBus 2552
7h 41m$38–87Fly Detroit to Chicago O'Hare International Airport
- Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)DTW - ORD
4h 11m$114–337Bus to Bishop International Airport, fly to Chicago O'Hare International Airport
- Take the bus from Detroit Bus Station to Flint
- Fly from Bishop International Airport (FNT) to Chicago O'Hare International Airport (ORD)FNT - ORD
4h 54m$45–279
Windsor to Chicago by bus
Questions & Answers
The cheapest way to get from Windsor to Chicago is to bus via Chicago which costs $35 - $90 and takes 7h 41m.
The fastest way to get from Windsor to Chicago is to fly which takes 3h 48m and costs $45 - $320.
Yes, there is a direct bus departing from Detroit Bus Station station and arriving at Chicago Bus Station station. Services depart four times a day, and operate every day. The journey takes approximately 6h 5m.
The distance between Windsor and Chicago is 288 miles. The road distance is 286.1 miles.
The best way to get from Windsor to Chicago without a car is to bus which takes 6h 5m and costs $35 - $110.
The bus from Detroit Bus Station to Chicago Bus Station takes 6h 5m including transfers and departs four times a day.
Windsor to Chicago bus services, operated by Greyhound USA, depart from Detroit Bus Station.
The best way to get from Windsor to Chicago is to bus which takes 6h 5m and costs $35 - $110. Alternatively, you can train, which costs $45 - $140 and takes 6h 20m, you could also fly, which costs $45 - $320 and takes 3h 48m.
Windsor to Chicago bus services, operated by Greyhound USA, arrive at Chicago Bus Station.
Chicago is 1h behind Windsor. It is currently 5:43 PM in Windsor and 4:43 PM in Chicago.
What companies run services between Windsor, ON, Canada and Chicago, IL, USA?
Greyhound USA operates a bus from Detroit Bus Station to Chicago Bus Station 3 times a day. Tickets cost $35–85 and the journey takes 6h 5m. Flixbus USA also services this route twice daily. Alternatively, Amtrak operates a train from Detroit to Chicago Union Station 3 times a day. Tickets cost $45–130 and the journey takes 5h 6m.
- Website
- aa.com
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 46m
- When
- Every day
- Estimated price
- $30–230
Flights from Bishop International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $30–230
- Website
- delta.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 23m
- When
- Every day
- Estimated price
- $45–310
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 31m
- When
- Every day
- Estimated price
- $30–230
- Website
- southwest.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 15m
- When
- Every day
- Estimated price
- $45–310
- Website
- united.com
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 40m
- When
- Every day
- Estimated price
- $30–230
Flights from Bishop International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 44m
- When
- Every day
- Estimated price
- $30–230
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
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/
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 50m
- Frequency
- Twice daily
- Estimated price
- $35–110
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Chicago
- Ave. Duration
- 7h 15m
- Frequency
- Once daily
- Estimated price
- $35–85
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Flint
- Ave. Duration
- 1h 15m
- Frequency
- Once daily
- Estimated price
- $13–45
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Yes, the driving distance between Windsor to Chicago is 286 miles. It takes approximately 4h 43m to drive from Windsor to Chicago.
Book your Windsor to Chicago bus tickets online with Omio and FlixBus.
There are 1101+ hotels available in Chicago.