Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Downtown Greyhound Station | Pittsfield (Joseph Scelsi Intermodal) | No tags | ||||
| Bus | 537-517 W. Jackson Blvd | Pittsfield (Joseph Scelsi Intermodal) | No tags | ||||
| Bus | Chicago 95Th & Dan Ryan | Pittsfield (Joseph Scelsi Intermodal) | No tags | ||||
Greyhound + FlixBus | Bus | Downtown Greyhound Station | Pittsfield (Joseph Scelsi Intermodal) | No tags | ||||
| Bus | Downtown Greyhound Station | Pittsfield (Joseph Scelsi Intermodal) | No tags |
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
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Chicago to Pittsfield?
The cheapest bus tickets from Chicago to Pittsfield start from $129. The average price for this route is around $164. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Chicago to Pittsfield?
The average bus trip duration from Chicago to Pittsfield is 1d 9h, covering a distance of 737 miles (1188 km). The quickest bus can get you there in 1d 6h and is operated by Greyhound.
Which bus companies service the Chicago to Pittsfield route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the bus from Chicago to Pittsfield?
The earliest bus departs from Chicago to Pittsfield at 5:45am. And the latest bus departs at 11:50pm.
What are the CO₂ emissions for the bus trip from Chicago to Pittsfield?
A bus trip from Chicago to Pittsfield generates an estimated 30 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
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 $358 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
