- Chicago to Windsor trains
Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
![]() | Train | Chicago (Union Station), IL | Windsor Station | No tags | ||||
![]() | Train | Chicago (Union Station), IL | Windsor Station | No tags | ||||
![]() | Train | Chicago (Union Station), IL | Windsor Station | No tags | ||||
![]() | Train | Chicago (Union Station), IL | Windsor Station | No tags |
Get from Chicago to Windsor
The journey takes about 1 day, 57 minutes, and with fares starting at just £258, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5655 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at £258
Frequently asked questions about travelling from Chicago to Windsor, CT, US by train
Please note that timetables, routes, or operator details shown here may be updated or vary at the time of your journey.
How much does a train ticket cost from Chicago to Windsor?
The cheapest train tickets from Chicago to Windsor start from £258. The average price for this train route is around £258. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the train journey from Chicago to Windsor?
The average train journey time from Chicago to Windsor is 1d , covering a distance of 770 miles. The fastest train gets you there in 1d and is operated by Amtrak.
Which train operators serve the Chicago to Windsor route?
Several major train operators run on this route with 2 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Windsor?
The earliest train from Chicago to Windsor departs at 18:40. And the latest train departs at 18:40.






