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Cheap bus tickets from Chicago to Pittsfield

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Chicago to Pittsfield Bus Schedule

Is it better to travel by bus or train from Chicago to Pittsfield?

There are usually 1 daily train trips available from Chicago to Pittsfield.

Bus
Train
Avg. Price
Avg. Price
$140.39
Avg. Price
$204.00
Daily Trips
Daily Trips
2
Daily Trips
1
Duration
Duration
1d 8h 53m
Duration
18h 0m

Bus from Chicago to Pittsfield: Journey Information

There are 2 intercity buses per day from Chicago to Pittsfield. Traveling by bus from Chicago to Pittsfield usually takes around 33 hours and 11 minutes, but the fastest FlixBus US bus can make the trip in 28 hours and 15 minutes.

Distance737 mi (1186 km)
Shortest duration28h 15m
Cheapest price$118.96
Most frequent serviceFlixBus US
Bus lines1

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What bus companies travel from Chicago to Pittsfield?

There is one intercity bus company available to search and book on Wanderu that operates from Chicago to Pittsfield. FlixBus US is the one bus line that serves this route. Although it's the sole option, there are a couple of different scheduled times to choose from.

BusDaily TripsAvg. TimeAvg. Price
FlixBus US21d 9h 11m$151.45
  • FlixBus US is the American branch of German bus company FlixBus, known for providing sustainable, affordable, and modern bus travel. The company offers cheap bus tickets to popular urban destinations throughout the United States. FlixBus US buses include many amenities, including comfortable seats, free WiFi, power outlets at every seat, and an online portal for free entertainment. On average, FlixBus US operates 2 trips per day from Chicago to Pittsfield, and the average ticket for this route costs only .

Frequently asked questions about traveling by bus from Chicago to Pittsfield

The bus takes an average of 33 hours and 11 minutes to cover the 737 miles from Chicago to Pittsfield. However, the fastest bus only takes 28 hours and 15 minutes. It’s definitely on the longer side, so plan to get comfortable for a long road trip. Keep in mind that your actual bus may arrive earlier or later than scheduled, depending on whether there is more or less traffic than usual.

Friday is the busiest travel day for buses as people head from Chicago to Pittsfield for the weekend. If you are planning to travel on a Friday, you should make sure to book tickets well in advance as they may sell out.

On the other hand, Tuesday is typically the least busy day for bus travel on this route. If you’re looking for a little extra space, a Tuesday ticket is the way to go.

The first bus leaves at 5:00am and the last bus leaves at 12:00pm. To see the times for all buses from Chicago to Pittsfield, enter your specific travel dates in the search bar.

There are usually only 2 buses per day from Chicago to Pittsfield. However, neither bus offers direct service, so you will have to get off your original vehicle to transfer buses during the trip.

Need more travel options? Consider taking the train from Chicago to Pittsfield; ticket prices start at $195.00.

City Information

Chicago

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Pittsfield

Pittsfield, MA, US - PIT-0

Image credit: Unsplash

Pittsfield is the largest city in the Berkshires region, Massachusetts. It is famous for having iconic residents like the author of Moby Dick, Herman Melville, and Rev. Thomas Allen of the Revolutionary War. Pittsfield offers many outdoor activities, like hiking on the Ashuwillticook Rail Trail or skiing on a 750-foot mountain at Bousquet Mountain Ski Area. Campers can check out the Pittsfield State Forest, while Lake Onota offers a scenic view. There are also different areas for history in Pittsfield, like the Hancock Shaker Village, which features living history exhibits, and the Berkshire Museum offers natural history. The city is popular among young families due to its fun activities and green spaces.

Pittsfield's downtown is the cultural center of Massachusetts, boasting an exciting dining scene with bars, cafés, and live music. Local stores also look out for when shopping and fun events like the Pittsfield Photo Challenge and the Berkshire International Film Festival. The latest addition is the Stargaze LGBTQ+ Festival in August.

Six bus routes go to Pittsfield, all powered by Greyhound. There are plenty of train services as well, offered by Amtrak and Amtrak Lake Shore Limited. Within the city, the Berkshire Regional Transit Authority provides public transportation.

Station Information

Where does the bus leave from in Chicago?

Main departure station: Dan Ryan Bus Station

Chicago has two bus stations with service to Pittsfield.

All bus stations in Chicago:

  • Dan Ryan Bus Station

  • Bus Station - 630 W Harrison St

Where does the bus arrive in Pittsfield?

Main arrival station: Scelsi Transp Ctr - 1 Columbus Ave

All buses from Chicago arrive at one main station in Pittsfield.

All bus stations in Pittsfield:

  • Scelsi Transp Ctr - 1 Columbus Ave

Get around town with Moovit

Find the best way to get to and from any station in Pittsfield by public transit, courtesy of Moovit. Search now

Need a return trip from Pittsfield to Chicago?

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