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The cheapest and fastest trains from Chicago, IL to Pittsfield, MA
Showing times, prices and bookable tickets for Nov 04
- Cheapest price on Nov 04
- $382
- Average ticket price on Nov 04
- $382
- Fastest journey on Nov 04
- 19 h
- Average journey duration on Nov 04
- 19 h
- Trains on Nov 04
- 1
- Distance
- 1188 km
Cheap tickets
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 $382 if you buy it on the day, but the cheapest tickets can be found for only $382.
Fast trains
On Wed, Nov 04, we found 1 trains from Chicago, IL to Pittsfield, MA, including 1 direct services.
On Wed, Nov 04 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 Wed, Nov 04 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.
9:30 PM 19h00 Chicago, IL 4:30 PM Pittsfield, MA $382 1 One-way 0 transfers
9:30 PM 19h00 Chicago, IL 4:30 PM Pittsfield, MA $382 1 One-way 0 transfers
Journey information
Overview: Train from Chicago, IL to Pittsfield, MA
USAUSA
Trains from Chicago, IL to Pittsfield, MA run on average 2 times per day, taking around 17h 43m. Cheap train tickets for this journey start at $142 but you can travel from only $124 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 17h 26m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $124
Plan this route
Journey facts
- Distance738 miles (1188 km)
- Average train duration17h 43m
- Cheapest ticket price$142
- Trains per day2
- Direct trains1
- Fastest train17h 26m
- First train4:39 PM
- Last train9:30 PM
- Cheapest MonthOct
- Cheapest DaySun
- High SeasonJan - Mar
- Low SeasonApr - Jun
- Best time to book77 days
Understand & plan this route
Explore this journey
Book with confidence
- Why book with Omio?Compare options, payment & support
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $124
Frequently asked questions about your Chicago, IL to Pittsfield, MA trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Pittsfield, MA.
Train ticket prices from Chicago, IL to Pittsfield, MA can vary. The cheapest ticket starts at $142, while the average price is around $229.
The train from Chicago, IL to Pittsfield, MA takes 17h 26m and runs 2 per day.
The first train from Chicago, IL to Pittsfield, MA leaves at 4:39 PM.
The distance by train from Chicago, IL to Pittsfield, MA is 738 miles (1188 km).
The last train from Chicago, IL to Pittsfield, MA leaves at 9:30 PM.
Yes, there is a direct train from Chicago, IL to Pittsfield, MA. This service operates 1 times per day, provided by Amtrak.
Live departures
Chicago, IL to Pittsfield, MA train times
The table below shows live departures for Chicago, IL to Pittsfield, MA trains for today, Tuesday, November 3. You can also manually refresh the results below to see updated train journeys.
Last updated at
| 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
Train companies
Train companies from Chicago, IL to Pittsfield, MA
Trains from Chicago, IL to Pittsfield, MA with Amtrak. Night trains available on this route with Amtrak. High-speed trains available on this route with Amtrak. Use the details below to compare onboard facilities.
Amtrak
About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Amtrak Duration
17h 26m
Cheapest Amtrak Price
$142
Amtrak frequency
2 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Companies, tickets, and onboard amenities between Chicago, IL and Pittsfield, MA
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
Yes, there is a high-speed train from Chicago, IL to Pittsfield, MA.
Yes, there is a night train from Chicago, IL to Pittsfield, MA.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
Complete guide to Pittsfield, MA
Things to do in Pittsfield, MA
Discover the best of Pittsfield, MA — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Pittsfield, MA trip today.
- Recommended
The Mount
Historic house museum in nearby Lenox presenting author Edith Wharton’s home, gardens, and design-focused exhibitions.
- Recommended
Ventfort Hall Mansion and Gilded Age Museum
Gilded Age museum inside Ventfort Hall with exhibits on regional history, domestic life, and the Berkshires’ summer estates.
- Recommended
Upstreet Cultural District
Downtown Pittsfield district with shops, public art, theaters, and event spaces, ideal for walking and experiencing local life.
- Recommended
Burbank Park on Onota Lake
Large city park with ponds, trails, athletic fields, and mountain views, popular for walks, picnics, and seasonal events.
- Recommended
Berry Pond and Balance Rock
Wooded reservation with hiking trails and a summit observation tower offering broad views over Pittsfield and the Berkshires.
New England Clam Chowder
New England clam chowder is a creamy soup of clams, potatoes, and salt pork. It is a Berkshire favorite in all seasons and a classic regional staple.
Lobster Roll
Lobster roll features chilled lobster meat in a toasted split-top bun, often with light mayo. It is a beloved New England summer seafood classic.
- Gluten-free
Johnnycake
Johnnycake is a cornmeal griddle cake rooted in early New England cooking. It is valued for its simple heritage ingredients and regional tradition.
Dotty's Coffee and Bakery
Long-running breakfast and lunch diner loved for pancakes, omelets, and classic American comfort food in an easygoing setting.
Methuselah Bar and Lounge
Lively downtown restaurant known for wood-fired pizzas, pasta, and a stylish but relaxed setting inside Hotel on North.
District Kitchen and Bar
Popular casual spot serving creative burgers, comfort food, and local beer in a friendly modern pub atmosphere.
US Dollar ($)
Moderate for a small US city: lodging and dining are below major metros, but car travel is common and transit is limited.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-35 per person for a restaurant meal.
- Fine dining
- $45+ per person for upscale dining.
- Coffee
- $3-6 for a regular coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, and 10-15% for taxis. Cafes often have tip jars or card prompts.
Plan your visit to Pittsfield, MA
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Pittsfield, MA.
The train journey from Chicago, IL to Pittsfield, MA offers scenic views, especially as it travels through the rolling hills and lush forests of upstate New York and Massachusetts, providing passengers with picturesque landscapes throughout the ride.
Popular day trips by train from Pittsfield, MA include Springfield, MA, Hartford, CT.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Pittsfield, MA, travelers should be mindful of typical urban safety concerns such as petty theft and vehicle break-ins, especially in busy areas or parking lots. It is advisable to stay alert in crowded places and avoid poorly lit streets at night. While there are no widespread reports of specific scams targeting visitors, travelers should be cautious of common scams like overcharging by taxis or unfamiliar vendors. Using reputable transportation services and securing personal belongings can help ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
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.
Yes, you can take the train from Chicago, IL to Pittsfield, MA.
popular train stations
Popular train stations from Chicago, IL to Pittsfield, MA
Most Chicago, IL to Pittsfield, MA trains use the Union Station to Pittsfield Station station pair. Use this guide to compare Chicago, IL and Pittsfield, MA train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Departure train stations in Chicago
Arrival train stations in Pittsfield
Which Chicago, IL station do trains to Pittsfield, MA leave from?
Trains from Chicago, IL to Pittsfield, MA leave from Union Station. The station is 1 miles (3 km) from Chicago, IL city centre at 225 South Canal Street, Chicago, IL 60606, USA.
Union Station225 South Canal Street, Chicago, IL 60606, USA+1 800-872-7245
City-centre transport
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · $4 · every ~13 min
Union Station train station facilities and services
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food and drink
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Wi-Fi and ATMs
Free. ATMs are available in the train station.
Tickets and information
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Union Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Union Station: Parking, Taxis, WC.
Bike and car services
Available at Union Station: Bike Parking, Car Rental.
Accessibility
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Shops, hotels and contact
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Which Pittsfield, MA station do trains from Chicago, IL arrive at?
Trains from Chicago, IL to Pittsfield, MA arrive at Pittsfield Station. Pittsfield Station is 0 miles (1 km) from Pittsfield, MA city centre.
Pittsfield Station1 Columbus Ave, Pittsfield, MA 01201, USA+1 800-872-7245
Pittsfield Station train station facilities and services
Pittsfield Station has practical services for this route, including Dining and Accessibility.
Food and drink
Food and drink options are available at Pittsfield Station.
Accessibility
Accessibility facilities are available at Pittsfield Station.
Train stations for Chicago, IL to Pittsfield, MA
Check train stations information for Chicago, IL and Pittsfield, MA, including where trains depart and arrive on this route.
The train station in Chicago, IL that goes to Pittsfield, MA is Union Station, which connects to Pittsfield Station.
Most popular train connections from Chicago, IL
Most popular trains to and from Pittsfield, MA and Chicago, IL
Most popular train connections to Pittsfield, MA
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