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 a good way to reach Pittsfield. The journey takes about 1 day, 9 hours 45 minutes, and with fares starting at just $187, 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
Based on 87394 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the WiFi. Greyhound ticket prices on this trip start at $199
Frequently asked questions about travelling from Chicago to Pittsfield by bus
What is the travel distance from Chicago to Pittsfield?
The distance between Chicago and Pittsfield is approximately 1186 km (736 miles).
What are the departure and arrival locations for buses traveling from Chicago to Pittsfield?
Buses departing from Downtown Greyhound Station in Chicago will take you to Joseph Scelsi Intermodal Transportation Center in Pittsfield.
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 $437To 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 $437 to $558 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 $437 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
