Compare 2 ways to go from Pittsfield to Chicago.
Busbud recommends taking the train from Pittsfield to ChicagoAmong the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 18 hours 30 minutes and with fares starting at just $195, it presents an excellent value for a comfortable ride.
Bus Pittsfield to Chicago: Trip Overview
Compare bus companies
Pittsfield to Chicago Bus
With Busbud, comparing and booking tickets for a bus from Pittsfield to Chicago is a breeze. Browse through an extensive selection of bus fares and bus schedules to find the best deals.
We make it our job to connect you with the most dependable bus companies that cover bus service from Pittsfield to Chicago.
From cheap bus tickets to more luxurious buses traveling from Pittsfield to Chicago, we offer a wide range of bus services to best suit your needs depending on how much your budget is.
Where are the popular stops in Pittsfield and Chicago?
Frequently asked questions for your trip Pittsfield - Chicago
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Pittsfield to Chicago was searched and found on May 6, 2025 with a price of $173To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Pittsfield to Chicago, as early as possible.
About Bus Travel
Bus Travel Tips
Meet and talk to locals at the bus stations while traveling from Pittsfield to Chicago.There is no better way to get inside travel information while exploring a new city than to go straight to its people.
From miles long of beauteous natural landscapes to impressive man-crafted sights, you're bound to be in for a visual treat on your bus trip from Pittsfield to Chicago.
Taking the bus creates the smallest carbon footprint compared to other modes of transport. Not to mention that buses will allow you to discover scenic gems from Pittsfield to Chicago that are otherwise impossible to come by with a plane.
Make a music playlist for your bus ride from Pittsfield to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!
One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.
The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.
Top traveled bus routes
Why choose Busbud?
The Best Way To Book Bus and Train Tickets
Busbud.com makes it easy for you to find, compare and book city-to-city bus tickets, all over the world. We save you the extra trip to the bus station. With several language and currency options available, Busbud seeks to cater to international bus travelers no matter where they are in the world. With Busbud, you can buy tickets with confidence. We ensure that you make the most out of your bus trip by partnering up with reliable bus companies from all around the world such as Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.
People from around the world trust Busbud
Popular Buses Connecting Pittsfield
Buses Leaving from Pittsfield
- Bus from Pittsfield to Albany
- Bus Pittsfield - Boston
- Pittsfield - Chicago
- Bus from Pittsfield to New York
- Bus Pittsfield - Springfield
- Pittsfield - Worcester
- Bus from Pittsfield to Schenectady
- Bus Pittsfield - Hartford
- Pittsfield - Hudson
- Bus from Pittsfield to Atlantic City
- Bus Pittsfield - Framingham
- Pittsfield - Philadelphia
- Bus from Pittsfield to Providence
- Bus Pittsfield - Lee
Buses Going to Pittsfield
- Bus from Albany to Pittsfield
- Bus Worcester - Pittsfield
- Stockbridge - Pittsfield
- Bus from New York to Pittsfield
- Bus Boston - Pittsfield
- Providence - Pittsfield
- Bus from Springfield to Pittsfield
- Bus Hartford - Pittsfield
- Poughkeepsie - Pittsfield
- Bus from Bennington to Pittsfield
- Bus Schenectady - Pittsfield