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, 16 hours 50 minutes, and with fares starting at just $176, it presents an excellent value for a comfortable ride.
Where are the popular train stations and stops in Chicago and Pittsfield?
Train companies
Based on 5733 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 $108
Frequently asked questions about travelling from Chicago to Pittsfield 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 Chicago to Pittsfield?
The cheapest train tickets from Chicago to Pittsfield start at $108. The average price for this train route is around $266. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Chicago to Pittsfield?
The average train trip from Chicago to Pittsfield takes 18h and covers 1187 km. The quickest train gets you there in 18h and is operated by Amtrak.
Which train operators serve the Chicago to Pittsfield route?
Several major train operators serve this route, with 1 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Pittsfield?
The earliest train from Chicago to Pittsfield departs at 9:30pm. The latest train departs at 9:30pm.
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 Jan 11, 2026 with a price of $232To 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.
