Next train departures
| 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 | Cheapest | ||||
NextGen Acela + Amtrak | Train | Stamford Station | Chicago (Union Station), IL | Fastest |
Last refresh of the prices: Today at 10:47 AM EST.
Compare 2 ways to go 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 $156, 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 5614 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 WiFi. Amtrak ticket prices on this trip start at $306
Frequently asked questions about travelling from Stamford, CT, US to Chicago by train
How much does a cheap train ticket from Stamford to Chicago cost?
The average train ticket price from Stamford to Chicago is $587. The best way to find cheap train tickets from Stamford to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the trip from Stamford to Chicago?
A train trip between Stamford and Chicago is around 23h 50m, although the fastest train will take about 22h 17m. This is the time it takes to travel the 1180 km that separates the two cities.
How many daily trains are there between Stamford and Chicago?
The number of trains from Stamford to Chicago can differ depending on the day of the week. On average, there are 3. Some trains are direct while others include transferring trains. Simplify your train trip from Stamford to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Stamford to Chicago?
When taking the train from Stamford to Chicago, you can travel comfortably and safely with Amtrak.
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 Nov 29, 2025 with a price of $421To 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 $421 to $1,738 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 $922 which is on 2025-11-30.
Top Travelled Train Routes
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