There are 9 ways to get from Windsor, Ontario Station to Chicago by bus (Greyhound, Flixbus), train (Amtrak), car, plane, bus (Amtrak), bus, or train
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 Stationbus Greyhound US0160
6h 30m$40–85Train (Amtrak)
- Take the train from Detroit to Chicago Union Stationtrain Wolverine
6h 36m$92–192Drive 283 mi
- Drive from Windsor, Ontario Station to Chicagocar 283 mi
4h 44m$52–75Fly Detroit to Chicago Midway International Airport
- Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane DTW - MDW
4h 14m$134–467Bus via Dearborn (Amtrak)
- Take the bus from Dearborn to Chicago Union Stationbus Amtrak Thruway Connecting Service
7h 2m$92–132Fly Detroit to Chicago O'Hare International Airport
- Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)plane DTW - ORD
4h 34m$134–657Bus to Bishop International Airport, fly to Chicago O'Hare International Airport
- Take the bus from Detroit Bus Station to Flintbus
- Fly from Bishop International Airport (FNT) to Chicago O'Hare International Airport (ORD)plane FNT - ORD
5h 16m$47–261Bus to Cleveland-Hopkins International Airport, fly to Chicago Midway International Airport
- Take the bus from Detroit Bus Station to Cleveland Bus Stationbus
- Fly from Cleveland-Hopkins International Airport (CLE) to Chicago Midway International Airport (MDW)plane CLE - MDW
6h 46m$89–434Fly Detroit to South Bend, train
- Fly from Detroit (DTW) to South Bend (SBN)plane DTW - SBN
- Take the train from South Bend Airport to Van Buren St.train
6h 26m$85–517
Windsor, Ontario Station to Chicago by foot, bus, and train (Amtrak)
Questions & Answers
The cheapest way to get from Windsor, Ontario Station to Chicago is to bus which costs $40 - $85 and takes 6h 30m.
The fastest way to get from Windsor, Ontario Station to Chicago is to fly which takes 4h 14m and costs $130 - $470.
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.
No, there is no direct train from Windsor, Ontario Station to Chicago station. However, there are services departing from Detroit and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 6h 36m.
The distance between Windsor, Ontario Station and Chicago is 289 miles. The road distance is 284.6 miles.
The best way to get from Windsor, Ontario Station to Chicago without a car is to bus which takes 6h 30m and costs $40 - $85.
The bus from Detroit Bus Station to Chicago Bus Station takes 6h 5m including transfers and departs four times a day.
Windsor, Ontario Station to Chicago bus services, operated by Greyhound USA, depart from Detroit Bus Station.
Windsor, Ontario Station to Chicago train services, operated by Amtrak, depart from Detroit station.
The best way to get from Windsor, Ontario Station to Chicago is to bus which takes 6h 30m and costs $40 - $85. Alternatively, you can train, which costs $90 - $200 and takes 6h 36m, you could also fly, which costs $130 - $470 and takes 4h 14m.
What companies run services between Windsor, Ontario Station, 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 $40–85 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 $90–190 and the journey takes 5h 6m.
- Website
- southwest.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 11m
- When
- Every day
- Estimated price
- $50–340
Flights from Cleveland-Hopkins International Airport to Chicago Midway International Airport
- Ave. Duration
- 1h 14m
- When
- Every day
- Estimated price
- $60–380
- Website
- delta.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 19m
- When
- Every day
- Estimated price
- $50–340
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $40–300
Flights from Cleveland-Hopkins International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 15m
- When
- Every day
- Estimated price
- $60–380
Flights from Detroit to South Bend
- Ave. Duration
- 1h 5m
- When
- Every day
- Estimated price
- $70–500
- Website
- aa.com
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 42m
- When
- Every day
- Estimated price
- $40–300
Flights from Bishop International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 39m
- When
- Every day
- Estimated price
- $35–240
- Website
- united.com
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 31m
- When
- Every day
- Estimated price
- $40–300
Flights from Bishop International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $35–240
Rome2Rio's guide to Amtrak
Contact DetailsContact 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
- $90–190
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $40–85
- Website
- https://www.greyhound.com/
Bus from Detroit Bus Station to Cleveland Bus Station
- Ave. Duration
- 3h 10m
- Frequency
- Twice daily
- Estimated price
- $24–50
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 50m
- Frequency
- Twice daily
- Estimated price
- $45–80
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Flint
- Ave. Duration
- 1h 10m
- Frequency
- Twice daily
- Estimated price
- $9–17
- Schedules at
- flixbus.com
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Dearborn to Chicago Union Station
- Ave. Duration
- 5h 9m
- Frequency
- Once a week
- Estimated price
- $90–130
- Website
- https://www.amtrak.com/home.html
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More Questions & Answers
Windsor, Ontario Station to Chicago bus services, operated by Greyhound USA, arrive at Chicago Bus Station.
Chicago is 1h behind Windsor, Ontario Station. It is currently 4:50 AM in Windsor, Ontario Station and 3:50 AM in Chicago.
Windsor, Ontario Station to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Windsor, Ontario Station to Chicago is 285 miles. It takes approximately 4h 44m to drive from Windsor, Ontario Station to Chicago.
There are 1328+ hotels available in Chicago.