The cheapest and fastest trains from Chicago, IL to Pittsfield, MA
Cheapest price
$314
Average price
$314
Fastest journey
18 h
Average duration
18 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 $314 if you buy it on the day, but the cheapest tickets can be found for only $314.
Of the 1 trains that leave Chicago, IL for Pittsfield, MA on Sat, Jun 27, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Jun 27 the direct trains cover the 1188 km distance in an average of 18 h but if you time it right, some trains will get you there in just 18 h .
On Sat, Jun 27 the slowest trains will take 18 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.
2:30 AM18h00Chicago, IL8:30 PMPittsfield, MA$3141One-way0 transfers
2:30 AM18h00Chicago, IL8:30 PMPittsfield, MA$3141One-way0 transfers
Travel Information
Compare train, bus, and flight 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 $125. For those with little time consider booking a flight which can get you there in 2h 12m. The ticket price range depends on the travel mode: a bus costs an average of $125, and a train costs an average of $261.
Distance: 738 miles (1188 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$539 Average price | $429 Average price | $138 Average price Cheapest | $173 Average price (fuel + tolls) |
18h 30m Average total duration 18h 0m Onboard + 30m Additional time* | 5h 12m Average total duration Fastest 2h 12m Onboard + 3h 0m Additional time* | 42h 20m Average total duration 41h 50m Onboard + 30m Additional time* | 12h 59m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Pittsfield, MA:
A bus is $290 (€238) less than a flight for this route with tickets for a flight from Chicago, IL to Pittsfield, MA costing on average $429 (€351).
A bus is $401 (€328) less than a train for this route with tickets for a train from Chicago, IL to Pittsfield, MA costing on average $539 (€441).
Other travel options to Pittsfield, MA take longer:
Train takes on average 18h 0m.
Bus takes on average 41h 50m.
Tickets start at around $539 (€441) compared to roughly $173 (€141) in fuel and tolls — a saving of about $-366.47 (€-299.94). The journey takes 18h 0m versus 12h 59m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Live departures
Chicago, IL to Pittsfield, MA train times
The table below shows live departures for Chicago, IL to Pittsfield, MA trains for today, Saturday, June 20. 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 | |
| Sunday, June 21 | |||||
![]() | 2:30 AM Chicago, IL | 18h00 | 8:30 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, bus, or flight
Compare train, bus, and flight 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.
Jun 21
Jun 22
Jun 23
Jun 24
Jun 25
Jun 26
Jun 27
Journey information
Overview: Train from Chicago, IL to Pittsfield, MA
Trains from Chicago, IL to Pittsfield, MA run on average 2 times per day, taking around 18h 0m. Cheap train tickets for this journey start at $261 (€213) but you can travel from only $125 (€102) by bus.
There are 1 trains per day. The earliest train runs at 16:39, the last at 21:30. The fastest train covers the 738 miles (1188 km) distance in 18h 0m.
Distance 738 miles (1188 km) |
Average train duration 18h 0m |
Cheapest ticket price $261 (€213) |
Trains per day 2 |
Direct trains 1 |
Fastest train 18h 0m |
First train 4:39 PM |
Last train 9:30 PM |
Cheapest Month Oct |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 77 days |
Train companies: Amtrak from Chicago, IL to Pittsfield, MA trainsAmtrak trains will get you between Chicago, IL and Pittsfield, MA from $125 (€102). 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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