Previously seen journeys
| 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 travel from Chicago to Pittsfield
Among the sustainable travel choices, the train stands out as a good way to reach Pittsfield. The journey takes about 18 hours and with fares starting at just R 2 223, 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
- B
Chicago O'Hare International Airport
- 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 87431 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 Wi-Fi. Greyhound ticket prices on this trip start at R 2 337
Frequently asked questions about travelling from Chicago to Pittsfield by bus
Please note that timetables, routes, or operator details shown here may be updated or differ 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 at R 2 225. The average price for this route is around R 2 873. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Chicago to Pittsfield?
The average bus journey time from Chicago to Pittsfield is 1d 10h, covering a distance of 1188 km. The fastest bus gets you there in 1d 6h and is operated by Greyhound.
Which bus companies service the Chicago to Pittsfield route?
Several major bus companies operate on this route with 4 buses 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 05:25. And the latest bus departs at 23:50.
What are the CO₂ emissions for the bus trip from Chicago to Pittsfield?
A bus trip from Chicago to Pittsfield produces an estimated 30 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
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 13 Dec 2025 with a price of R 2 049To 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.
