The cheapest and fastest trains from Chicago, IL to Pittsfield, MA
Cheapest price
$257
Average price
$257
Fastest journey
19 h
Average duration
19 h
Trains per day
1
Distance
1188 km
The best way to find a cheap train ticket from Chicago, IL to Pittsfield, MA is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Pittsfield, MA will cost around $257 if you buy it on the day, but the cheapest tickets can be found for only $257.
Of the 1 trains that leave Chicago, IL for Pittsfield, MA on Fri, Nov 07, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Nov 07 the direct trains cover the 1188 km distance in an average of 19 h but if you time it right, some trains will get you there in just 19 h .
On Fri, Nov 07 the slowest trains will take 19 h and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


Travel Information
Compare train and bus for Chicago, IL to Pittsfield, MA
Omio recommends booking the train as it is the most popular option from Chicago, IL to Pittsfield, MA among Omio's users. If you are prioritising price take the bus with prices starting from €198. For those with little time consider booking a train which can get you there in 18h 0m. The ticket price range depends on the travel mode: a bus costs an average of €198, and a train costs an average of €211.
Distance: 738 miles (1188 km)
Compare train with
Most popular Train | Bus |
|---|---|
€211 Average price | €198 Average price Cheapest |
18h 30m Average total duration Fastest 18h 0m Onboard + 30m Additional time* | 42h 55m Average total duration 42h 25m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Live departures
Chicago, IL to Pittsfield, MA train times
The table below shows live departures for Chicago, IL to Pittsfield, MA trains for today, Thursday, November 6. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:30 PM Chicago, IL | 19h00 | 4:30 PM Pittsfield, MA | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Pittsfield, MA by train or bus
Compare train and bus prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Nov 07
Nov 08
Nov 09
Nov 10
Nov 11
Nov 12
Nov 13
Journey information
Overview: Train from Chicago, IL to Pittsfield, MA
Distance 738 miles (1188 km) |
Average train duration 18h 0m |
Cheapest ticket price $259 (€211) |
Trains per day 2 |
Fastest train 19h 0m |
First train 16:39 |
Last train 21:30 |
Key Takeaways
Train Ticket Prices
- Budget Options: Train tickets from Chicago, IL to Pittsfield, MA start from as low as $259 (€211) if booked well in advance.
- Standard Fares: Typically, trains cost $259 (€211) depending on the train type and class.
Train companies: Amtrak from Chicago, IL to Pittsfield, MA trainsAmtrak trains will get you between Chicago, IL and Pittsfield, MA from $243 (€198). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Chicago, IL to Pittsfield, MA
Find answers to the most common questions about traveling from Chicago, IL to Pittsfield, MA by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Pittsfield, MA, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Chicago, IL to Pittsfield, MA
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Pittsfield, MA
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