Next train departures
| 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 | CheapestFastest | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags | ||||
| Train | Chicago (Union Station), IL | Joseph Scelsi Intermodal Transportation Center | No tags |
Last refresh of the prices: Last Sunday at 6:15 PM CST.
Compare 2 ways to travel from Chicago to Pittsfield
Among the sustainable travel choices, the train stands out as a good way to reach Pittsfield. The journey takes about 18 hours and with fares starting at just R 2 223, 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 5639 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 2 223
Frequently asked questions about travelling from Chicago to Pittsfield 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 Chicago to Pittsfield?
The cheapest train tickets from Chicago to Pittsfield start from R 2 223. The average price for this train route is around R 2 670. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Chicago to Pittsfield?
The average train journey time from Chicago to Pittsfield is 18h, covering a distance of 1187 km. The quickest train can get you there in 18h and is operated by Amtrak.
Which train operators serve the Chicago to Pittsfield route?
Several major train operators run on 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 21:30. And the latest train departs at 21:30.
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 10 Dec 2025 with a price of R 2 127To 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.
What's the cheapest way to go from Chicago to Pittsfield?
The train is the cheapest travel choice for this destinationThe best way to travel between Chicago and Pittsfield is by train. By choosing the train, you'll get to save some money as you travel to your destination, as ticket prices cost R 2 670 on average. If you're on a budget, you'll find cheap tickets from R 2 223. If you're looking for the fastest way to get to Pittsfield, choose the train, as it will take you from Chicago to Pittsfield in about 18h – that's the fastest way to get there!
