Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
FlixBus + Greyhound Lines, Inc. | Bus | Chicago 95Th & Dan Ryan | Pittsfield (Joseph Scelsi Intermodal) | CheapestFastest |
Last refresh of the prices: Last Sunday at 8:27 PM CST.
Compare 2 ways to go from Chicago to Pittsfield
Among the sustainable travel choices, the bus stands out as the good way to reach Pittsfield. The journey takes about 1 day, 9 hours 45 minutes and with fares starting at just $129, it presents an excellent value for a comfortable ride.
Where are the popular stops in Chicago and Pittsfield?
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Stops in Pittsfield
- A
Joseph Scelsi Intermodal Transportation Center
1 Columbus Ave, Pittsfield, MA 01201, USA
Compare bus companies
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Frequently asked questions about traveling from Chicago to Pittsfield by bus
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Pittsfield was searched and found on Nov 30, 2025 with a price of $302To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Pittsfield, as early as possible.
You can expect to pay from $302 to $385 for a bus ticket from Chicago to Pittsfield based on the last 2 days. You can expect to find the cheapest price for the trip at $302 which is on 2025-11-30.
What's the cheapest way to go from Chicago to Pittsfield?
The bus is the cheapest travel choice for this destination
