There are 9 ways to get from Chicago to Windsor by train (Amtrak), bus (Amtrak), car, subway, plane, bus (Greyhound, 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 Dearborntrain Wolverine
5h 30m$112–235Bus
cheapest- Take the bus from Chicago Bus Station to Detroit Bus Stationbus Greyhound US0160
6h 15m$55–110Bus via Dearborn Transit Center (Amtrak)
- Take the bus from Chicago Union Station to Dearbornbus Amtrak Thruway Connecting Service
5h 46m$124–167Drive 457.6 km
- Drive from Chicago to Windsorcar 457.6 km
4h 47m$91–131Subway to Chicago Midway International Airport, fly to Detroit
- Take the subway from Adams/Wabash to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Detroit (DTW)plane MDW - DTW
3h 53m$196–660Fly Chicago O'Hare International Airport to Detroit
- Fly from Chicago O'Hare International Airport (ORD) to Detroit (DTW)plane ORD - DTW
4h 22m$196–1,010Train to South Bend, fly to Detroit
- Take the train from Van Buren St. to South Bend Airporttrain
- Fly from South Bend (SBN) to Detroit (DTW)plane SBN - DTW
5h 24m$102–673Train to General Mitchell International Airport, fly to Detroit
- Take the train from Chicago Union Station to Milwaukeetrain
- Fly from General Mitchell International Airport (MKE) to Detroit (DTW)plane MKE - DTW
5h 22m$1,040–1,595Fly Chicago O'Hare International Airport to Bishop International Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Bishop International Airport (FNT)plane ORD - FNT
- Take the bus from Flint to Detroit Bus Stationbus
5h 48m$70–407
Chicago to Windsor by train and bus (Amtrak)
Questions & Answers
The cheapest way to get from Chicago to Windsor is to bus which costs $55 - $110 and takes 6h 15m.
The fastest way to get from Chicago to Windsor is to subway and fly which takes 3h 53m and costs $190 - $700.
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 15m.
No, there is no direct train from Chicago station to Windsor. However, there are services departing from Chicago Union Station and arriving at Dearborn via . The journey, including transfers, takes approximately 5h 30m.
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 30m and costs $110 - $240.
It takes approximately 5h 30m to get from Chicago to Windsor, including transfers.
Chicago to Windsor bus services, operated by Amtrak, depart from Chicago Union Station.
Chicago to Windsor train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Windsor is to train which takes 5h 30m and costs $110 - $240. Alternatively, you can bus via Dearborn Transit Center, which costs $120 - $170 and takes 5h 46m, you could also fly, which costs $190 - $1,100 and takes 4h 22m.
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 $100–240 and the journey takes 4h 47m. Alternatively, Amtrak operates a bus from Chicago Union Station to Dearborn twice a week. Tickets cost $120–170 and the journey takes 4h 47m.
- Website
- delta.com
Flights from Chicago Midway International Airport to Detroit
- Ave. Duration
- 1h 12m
- When
- Every day
- Estimated price
- $95–700
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 28m
- When
- Every day
- Estimated price
- $75–550
Flights from South Bend to Detroit
- Ave. Duration
- 1h 6m
- When
- Every day
- Estimated price
- $80–650
Flights from General Mitchell International Airport to Detroit
- Ave. Duration
- 1h 12m
- When
- Every day
- Estimated price
- $110–800
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 33m
- When
- Every day
- Estimated price
- $75–550
Flights from Chicago O'Hare International Airport to Bishop International Airport
- Ave. Duration
- 1h 21m
- When
- Every day
- Estimated price
- $55–380
- Website
- southwest.com
Flights from Chicago Midway International Airport to Detroit
- Ave. Duration
- 1h 11m
- When
- Every day
- Estimated price
- $95–700
Flights from General Mitchell International Airport to Detroit via Chicago Midway International Airport
- Ave. Duration
- 3h 2m
- When
- Saturday and Sunday
- Estimated price
- $120–850
- Website
- united.com
Flights from Chicago O'Hare International Airport to Detroit
- Ave. Duration
- 1h 33m
- When
- Every day
- Estimated price
- $75–550
Flights from Chicago O'Hare International Airport to Bishop International Airport
- Ave. Duration
- 1h 21m
- When
- Every day
- Estimated price
- $55–380
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Dearborn
- Ave. Duration
- 4h 47m
- Frequency
- 3 times a day
- Estimated price
- $100–240
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $30–75
- Website
- Amtrak
- Phone
- +1 888-968-7282
- Website
- Chicago Transit Authority
Subway from Adams/Wabash to Midway
- Ave. Duration
- 23 min
- Frequency
- Every 15 minutes
- Estimated price
- $3–7
- Website
- Chicago Transit Authority
- Schedules at
- Chicago Transit Authority Schedules & Routes
- Adult
- $3–7
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
- Ave. Duration
- 2h 4m
- Frequency
- Hourly
- Estimated price
- $18–20
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $18–20
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Bus from Chicago Union Station to Dearborn
- Ave. Duration
- 4h 47m
- Frequency
- Twice a week
- Estimated price
- $120–170
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 6h 15m
- Frequency
- 3 times a day
- Estimated price
- $55–110
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 7h 55m
- Frequency
- Twice daily
- Estimated price
- $55–95
- Schedules at
- Flixbus USA
Bus from Flint to Detroit Bus Station
- Ave. Duration
- 1h 15m
- Frequency
- Twice daily
- Estimated price
- $12–20
- Schedules at
- Flixbus USA
Want to know more about travelling around Canada
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
More Questions & Answers
Chicago to Windsor bus services, operated by Amtrak, arrive at Dearborn station.
Windsor is 1h ahead of Chicago. It is currently 4:03 PM in Chicago and 5:03 PM in Windsor.
Chicago to Windsor train services, operated by Amtrak, arrive at Dearborn station.
Yes, the driving distance between Chicago to Windsor is 458 km. It takes approximately 4h 47m to drive from Chicago to Windsor.
Book your Chicago to Windsor bus tickets online with Omio.
There are 429+ hotels available in Windsor.











