How much does a train ticket from Pittsfield to Chicago cost?

The average train ticket price from Pittsfield to Chicago is $155. The best way to find train tickets from Pittsfield 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 train trip from Pittsfield to Chicago?

A train trip between Pittsfield and Chicago is around 18h 30m, although the fastest train will take about 18h 30m. This is the time it takes to travel the 736 miles that separates the two cities.

How many daily trains are there between Pittsfield and Chicago?

The number of trains from Pittsfield to Chicago 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 Pittsfield to Chicago by comparing and selecting the train that fits you travel style and budget on Busbud.

Which train companies travel from Pittsfield to Chicago?

When taking the train from Pittsfield to Chicago, you can travel comfortably and safely with Amtrak.

What are the best sights and things to do in Chicago?

Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.

Train Pittsfield to Chicago from $258 | Refundable Tickets

Next train departures

Next departures for Pittsfield to Chicago on December 1
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	4:42pm	Joseph Scelsi Intermodal Transportation Center	18h 30m	10:12am	Chicago (Union Station), IL	CheapestFastest
Train	4:42pm	Joseph Scelsi Intermodal Transportation Center	18h 30m	10:12am	Chicago (Union Station), IL	No tags
Train	4:42pm	Joseph Scelsi Intermodal Transportation Center	18h 30m	10:12am	Chicago (Union Station), IL	No tags

Last refresh of the prices: Last Thursday at 9:34 AM EST.

Compare 2 ways to go from Pittsfield to Chicago

We recommend taking the train

Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 18 hours 30 minutes and with fares starting at just $155, it presents an excellent value for a comfortable ride.

1train per day

18h 30mAverage Duration

736 milesDistance

108kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$124 - $286	Average Duration1d 5h	CO₂ emissions 30kg CO₂e
Train	Average Price$155 - $155	Average Duration18h 30m	CO₂ emissions 108kg CO₂e

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

Pittsfield

A
Joseph Scelsi Intermodal Transportation Center
1 Columbus Ave, Pittsfield, MA 01201, USA
Visit page

Chicago

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

Train Companies

Amtrak

4/55,616 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5616 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 $155

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Pittsfield to Chicago by train

How much does a train ticket from Pittsfield to Chicago cost?
How long is the train trip from Pittsfield to Chicago?
How many daily trains are there between Pittsfield and Chicago?
Which train companies travel from Pittsfield to Chicago?
What are the best sights and things to do in Chicago?

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

11/28

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11/29

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Today

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12/01

$258

12/02

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12/03

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12/04

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12/05

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The cheapest trip from Pittsfield to Chicago was searched and found on Dec 1, 2025 with a price of $258

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Pittsfield to Chicago, as early as possible.

You can expect to pay from $258 to $339 for a train ticket from Pittsfield to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $258 which is on 2025-12-01.