The average train between Chicago and Windsor takes 8h 2m and the fastest train takes 5h 54m. The train service runs several times per day from Chicago to Windsor. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.
Trains run 3 times a day between Chicago and Windsor. The earliest departure is at 6:45 AM in the morning, and the last departure from Chicago is at 5:50 PM which arrives into Windsor at 7:54 AM. All services require a transfer at Detroit and take an average of 8h 2m. The schedules shown below are for the next available departures.

7h 9m • 1 change

6h 54m • 1 change
Arrives next day

14h 4m • 1 change

7h 9m • 1 change

6h 54m • 1 change
Arrives next day

14h 4m • 1 change

7h 9m • 1 change

6h 54m • 1 change
Arrives next day

14h 4m • 1 change

7h 9m • 1 change

6h 54m • 1 change
Arrives next day

14h 4m • 1 change
Want to know about travelling from Chicago to Windsor? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.
No, there is no direct train from Chicago to Windsor. However, there are services departing from Chicago station and arriving at Windsor station via Detroit. The journey, including transfers, takes approximately 8h 2m.
Chicago to Windsor train services, operated by Amtrak, depart from Chicago Union Station.
Chicago to Windsor train services, operated by Amtrak, arrive at Detroit station.
The distance between Chicago and Windsor is 383.4 km. The road distance is 456 km.
Amtrak operates a train from Chicago Union Station to Detroit 3 times a day. Tickets cost $100–240 and the journey takes 5h 20m.