- Chicago to Windsor trains
Previously seen trips
| 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 $336, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5655 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $336
Frequently asked questions about traveling from Chicago to Windsor, CT, US by train
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the train ticket from Chicago to Windsor?
The cheapest train tickets from Chicago to Windsor start from $336. The average price for this train route is around $336. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Chicago to Windsor?
The average train ride duration from Chicago to Windsor is 1d , covering a distance of 770 miles (1241 km). The quickest train can get you there in 1d and is operated by Amtrak.
Which train operators service the Chicago to Windsor route?
Several major train operators operate on this route with 2 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Windsor?
The earliest train departs from Chicago to Windsor at 6:40pm. And the latest train departs at 6:40pm.






