Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags |
Compare 2 ways to go from Chicago to Pittsfield
Among the sustainable travel choices, the bus stands out as a good way to reach Pittsfield. The journey takes about 1 day, 9 hours 45 minutes, and with fares starting at just $186, it presents an excellent value for a comfortable ride.
Where are the popular train stations and stops in Chicago and Pittsfield?
Chicago
- A
Union Station
225 S Canal St, Chicago, IL 60606, USA
Train companies
Based on 5607 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 $186
Frequently asked questions about travelling from Chicago to Pittsfield by train
How much does a cheap train ticket from Chicago to Pittsfield cost?
The average train ticket price from Chicago to Pittsfield is $388. The best way to find cheap train tickets from Chicago to Pittsfield 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 Chicago to Pittsfield?
A train trip between Chicago and Pittsfield is around 18h, although the fastest train will take about 18h. This is the time it takes to travel the 1186 km that separates the two cities.
How many daily trains are there between Chicago and Pittsfield?
The number of trains from Chicago to Pittsfield can differ depending on the day of the week. On average, there is 1. Some trains are direct while others have layovers. Simplify your train trip from Chicago to Pittsfield by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Pittsfield?
When taking the train from Chicago to Pittsfield, 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 Chicago to Pittsfield was searched and found on Nov 30, 2025 with a price of $373To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Pittsfield, as early as possible.
You can expect to pay from $373 to $1,610 for a train ticket from Chicago to Pittsfield based on the last 2 days. You can expect to find the cheapest price for the trip at $373 which is on 2025-11-30.
