View Current Travel Advisories

Trailways Bus Tickets
from Chicago, IL to Pittsfield, MA

Choose one way or round trip:
(*) indicates a required field
Type the date in date format 2 digit month slash 2 digit day slash 4 digit year or press tab to use the date picker pop up calendar

Travel made simple with Trailways

Unbeatable Prices

One of the best inventories of bus tickets in one place - with exclusive fares you won't find elsewhere.

Proven Reliability

On-time travel services - trust our reputation for reliable bus transportation.

Comfort and Convenience

Numerous upgraded buses with large leather recliners, free wi-fi, and power outlets for each seat.
Overview

About buses from Chicago, IL to Pittsfield, MA

Buses from Chicago, IL to Pittsfield, MA travel the 745mi (1198.96km) journey, taking approximately 1d, 5h, 35m. Usually, there is 1 bus operating per day. While the average ticket price for this journey is around $195.72, you can find the cheapest bus tickets for as low as $195.72.

  • Distance
    745mi (1198.96km)
  • Average trip duration
  • Average bus ticket price
    $195.72
  • Trips per day
    1
  • Top Carriers
    FlixBus

Bus Station Information for Pittsfield, MA

Pittsfield

Curbside Stop, use arrow keys or tab to explore more about this bus station

Pittsfield, MA 01201

Curbside Stop
Address
1 Columbus Ave. 
Pittsfield, MA 01201
Phone Number
(800) 858-8555
More Detailsabout Pittsfield Curbside Stop

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

City InformationforPittsfield, MA

Hop on a bus to Pittsfield, MA, where charming Berkshire beauty meets a delightful mix of arts and nature. Whether you’re a culture connoisseur or outdoor enthusiast, this town has an impressive spread of things to do without breaking the bank. Art lovers will find their paradise at the Berkshire Museum, where interactive exhibits invite curiosity, while music aficionados can tap their toes at the annual Tanglewood concerts. Or take a step into the past with Hancock Shaker Village; it’s a living history museum where time seems to stand still.

If Mother Nature’s your calling, the Berkshire Botanical Garden offers stunning blooms in all seasons, and there's plenty of hiking at Pittsfield State Forest with trails boasting jaw-dropping views. Strolling through the local shops and cozy cafés of downtown is perfect for those seeking laid-back leisure.

The vibrant arts scene and serene natural landscape make Pittsfield an ideal stop. Book your bus to Pittsfield, MA, and embrace the blend of culture and tranquility that defines this delightful town.

Frequently Asked Questions about the Bus Ride

Make your trip from Chicago to Pittsfield simple by taking the bus. Trailways gives you the cheap, fast fares you need when you're traveling. Comfort, convenience, and affordability. Buy your Pittsfield bus ticket today.