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 | Cheapest | ||||
| Train
| Windsor Station | Chicago (Union Station), IL | Fastest | ||||
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| 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 | ||||
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| Windsor Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Today at 10:57 AM EDT.
Get from Windsor to Chicago
The journey takes about 1 day, 5 hours 4 minutes, and with fares starting at just ₪722, it presents an excellent value for a comfortable ride.
Train Companies
Based on 6503 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained about the Wi-Fi. Amtrak ticket prices on this trip start at ₪722
Frequently asked questions about travelling from Windsor, CT, US to Chicago by train
Please note that timetables, routes, or operator details shown here may be updated or differ 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 ₪722. The average price for this train route is around ₪790. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Windsor to Chicago?
The average train journey time from Windsor to Chicago is 1d 5h, covering a distance of 1241 km. The quickest train can get you there in 1d 5h and is operated by Amtrak.
Which train operators serve the Windsor to Chicago route?
Several major train operators run on 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 04:41. And the latest train departs at 04:41.
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 24 Sept 2026 with a price of ₪849To 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 ₪849 to ₪3 188 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 ₪849, which is on 2026-09-24.
