Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Windsor Station | Chicago (Union Station), IL | CheapestFastest | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags | ||||
| Train | Windsor Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Today at 10:16 AM EDT.
Get from Windsor to Chicago
The journey takes about 1 day, 5 hours 4 minutes and with fares starting at just $298, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5832 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 $298
Frequently asked questions about traveling 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 from $298. The average price for this train route is around $349. 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 Windsor to Chicago?
The average train ride duration from Windsor to Chicago is 1d 5h, covering a distance of 770 miles (1241 km). The quickest train can get you there in 1d 5h and is operated by Amtrak.
Which train operators service the Windsor to Chicago route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the train from Windsor to Chicago?
The earliest train departs from Windsor to Chicago at 4:41am. And 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 28, 2026 with a price of $283To 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.
You can expect to pay from $283 to $1,246 for a train ticket from Windsor, CT, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $283 which is on 2026-06-28.
