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 | ||||
| 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: Last Saturday at 14:18 EDT.
Get from Windsor to Chicago
The journey takes about 1 day, 5 hours 4 minutes, and with fares starting at just NOK 1,131, it presents an excellent value for a comfortable ride.
Train Companies
Based on 6434 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 NOK 1,131
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 vary at the time of your journey.
How much does a train ticket cost from Windsor to Chicago?
The cheapest train tickets from Windsor to Chicago start from NOK 1,131. The average price for this train route is around NOK 3,690. Busbud recommends booking your tickets in advance for the best chance of getting 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 770 miles. The fastest train gets you there in 23h 19m 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 11:53.
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 18 Aug 2026 with a price of NOK 2,781To 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 NOK 2,781 to NOK 10,332 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 NOK 2,781, which is on 2026-08-18.
