Previously seen trips

Next departures for Chicago to Pittsfield on August 4
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location
Train	9:30pm	Chicago (Union Station), IL	18h	4:30pm	Joseph Scelsi Intermodal Transportation Center
Train	9:30pm	Chicago (Union Station), IL	18h	4:30pm	Joseph Scelsi Intermodal Transportation Center
Train	9:30pm	Chicago (Union Station), IL	18h	4:30pm	Joseph Scelsi Intermodal Transportation Center
Train	9:30pm	Chicago (Union Station), IL	18h	4:30pm	Joseph Scelsi Intermodal Transportation Center
Train	9:30pm	Chicago (Union Station), IL	18h	4:30pm	Joseph Scelsi Intermodal Transportation Center

Compare 2 ways to go from Chicago to Pittsfield

We recommend taking the bus

Among the sustainable travel choices, the Bus stands out as a good way to reach Pittsfield. The journey takes about 1 day, 6 hours 25 minutes and with fares starting at just CLP 115,313, it presents an excellent value for a comfortable ride.

5bus per day

1d 6hAverage Duration

736 milesDistance

30kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average PriceCLP 115,313 - CLP 250,431	Average Duration1d 6h	CO₂ emissions 30kg CO₂e
Train	Average PriceCLP 104,191 - CLP 262,179	Average Duration18h	CO₂ emissions 108kg CO₂e

Where are the popular train stations and stops in Chicago and Pittsfield?

Chicago

A
Union Station
225 S Canal St, Chicago, IL 60606, USA

Pittsfield

A
Joseph Scelsi Intermodal Transportation Center
1 Columbus Ave, Pittsfield, MA 01201, USA
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Train Companies

Amtrak

4.1/56,382 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wifi3.6

Based on 6382 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at CLP 104,191

US train companies:Amtrak, Amtrak Acela, Brightline

Frequently asked questions about traveling 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 from CLP 104,191. The average price for this train route is around CLP 214,099. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Chicago to Pittsfield?
The average train ride duration from Chicago to Pittsfield is 18h, covering a distance of 736 miles (1187 km). The quickest train can get you there in 18h and is operated by Amtrak.
Which train operators service the Chicago to Pittsfield route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Pittsfield?
The earliest train departs from Chicago to Pittsfield at 9:30pm. And 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.

Best price found

08/01

No data

08/02

No data

Today

CLP 210,487

08/04

CLP 210,487

08/05

CLP 156,443

08/06

No data

08/07

No data

08/08

No data

The cheapest trip from Chicago to Pittsfield was searched and found on Aug 5, 2026 with a price of CLP 156,443

To 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 CLP 156,443 to CLP 1,061,912 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 CLP 156,443 which is on 2026-08-05.