Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Price and booking link |
|---|---|---|---|---|---|---|---|
 | Train | Stamford Station | Chicago (Union Station), IL | ||||
| Train | Stamford Station | Chicago (Union Station), IL | ||||
| Train | Stamford Station | Chicago (Union Station), IL | ||||
| Train | Stamford Station | Chicago (Union Station), IL | ||||
| Train | Stamford Station | Chicago (Union Station), IL |
Compare 2 ways to go from Stamford to Chicago
Among the sustainable travel choices, the Train stands out as a good way to reach Chicago. The journey takes about 23 hours 46 minutes and with fares starting at just CLP 183,583, it presents an excellent value for a comfortable ride.
Where are the popular train stations and stops in Stamford, CT, US and Chicago?
Chicago
- A
Union Station
225 S Canal St, Chicago, IL 60606, USA
Train Companies
Based on 5818 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 CLP 183,583
Frequently asked questions about traveling from Stamford, 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 Stamford to Chicago?
The cheapest train tickets from Stamford to Chicago start from CLP 183,583. The average price for this train route is around CLP 361,308. 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 Stamford to Chicago?
The average train ride duration from Stamford to Chicago is 23h 46m, covering a distance of 730 miles (1178 km). The quickest train can get you there in 22h 17m and is operated by Amtrak.
Which train operators service the Stamford to Chicago route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the train from Stamford to Chicago?
The earliest train departs from Stamford to Chicago at 7:04am. And the latest train departs at 9:55pm.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Stamford, CT, US to Chicago was searched and found on Jun 9, 2026 with a price of CLP 209,358To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Stamford, CT, US to Chicago, as early as possible.
You can expect to pay from CLP 209,358 to CLP 1,069,745 for a train ticket from Stamford, CT, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at CLP 209,358 which is on 2026-06-09.
