Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Stamford Station | Chicago (Union Station), IL | No tags | ||||
| Train | Stamford Station | Chicago (Union Station), IL | No tags | ||||
| Train | Stamford Station | Chicago (Union Station), IL | No tags | ||||
| Train | Stamford Station | Chicago (Union Station), IL | No tags | ||||
| Train | Stamford Station | Chicago (Union Station), IL | No tags |
Compare 2 ways to travel from Stamford to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 5 hours 50 minutes and with fares starting at just R 1 871, 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 5641 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 R 3 942
Frequently asked questions about travelling from Stamford, 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 Stamford to Chicago?
The cheapest train tickets from Stamford to Chicago start from R 3 942. The average price for this train route is around R 7 720. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Stamford to Chicago?
The average train journey time from Stamford to Chicago is 23h 46m, covering a distance of 1178 km. The quickest train can get you there in 22h 17m and is operated by Amtrak.
Which train operators serve the Stamford to Chicago route?
Several major train operators run on this route, with 4 trains available per day.
What are the earliest and latest departure times for the train from Stamford to Chicago?
The earliest train from Stamford to Chicago departs at 07:04. And the latest train departs at 21:55.
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 13 Dec 2025 with a price of R 4 775To 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 R 4 775 to R 36 186 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 R 4 775, which is on 2025-12-13.
