Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Price and booking link |
|---|---|---|---|---|---|---|---|
 | Train | Windsor Station | Chicago (Union Station), IL | ||||
| Train | Windsor Station | Chicago (Union Station), IL | ||||
| Train | Windsor Station | Chicago (Union Station), IL |
Get from Windsor to Chicago
The journey takes about 1 day, 5 hours 4 minutes, and with fares starting at just CLP 278,549, it presents an excellent value for a comfortable ride.
Train companies
Based on 5830 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 CLP 278,549
Frequently asked questions about travelling from Windsor, CT, US to Chicago 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 Windsor to Chicago?
The cheapest train tickets from Windsor to Chicago start at CLP 278,549. The average price for this train route is around CLP 327,048. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Windsor to Chicago?
The average train trip from Windsor to Chicago takes 1d 5h and covers 1241 km. The quickest train gets you there in 1d 5h and is operated by Amtrak.
Which train operators serve the Windsor to Chicago route?
Several major train operators serve this route, with 1 trains available per day.
What are the earliest and latest departure times for the train from Windsor to Chicago?
The earliest train from Windsor to Chicago departs at 4:41am. The latest train departs at 4:41am.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Windsor, CT, US to Chicago was searched and found on Jun 23, 2026 with a price of CLP 329,887To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Windsor, CT, US to Chicago, as early as possible.
