Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | Pittsfield (Joseph Scelsi Intermodal) | 537-517 W. Jackson Blvd | No tags | ||||
| Bus | Pittsfield (Joseph Scelsi Intermodal) | Chicago 95Th & Dan Ryan | No tags | ||||
| Bus | Pittsfield (Joseph Scelsi Intermodal) | Downtown Greyhound Station | No tags | ||||
| Bus | Pittsfield (Joseph Scelsi Intermodal) | 537-517 W. Jackson Blvd | No tags | ||||
| Bus | Pittsfield (Joseph Scelsi Intermodal) | Chicago 95Th & Dan Ryan | No tags |
Compare 2 ways to travel from Pittsfield to Chicago
Among the sustainable travel choices, the Bus stands out as a good way to reach Chicago. The journey takes about 1 day, 6 hours 5 minutes and with fares starting at just R 1 806, it presents an excellent value for a comfortable ride.
Where are the popular stops in Pittsfield and Chicago?
Stops in Pittsfield
- A
Joseph Scelsi Intermodal Transportation Center
1 Columbus Ave, Pittsfield, MA 01201, USA
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
Compare bus companies
Frequently asked questions about travelling from Pittsfield to Chicago 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 Pittsfield to Chicago?
The cheapest bus tickets from Pittsfield to Chicago start at R 1 806. The average price for this route is around R 2 079. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Pittsfield to Chicago?
The average bus journey time from Pittsfield to Chicago is 1d 6h, covering a distance of 1188 km. The fastest bus gets you there in 18h 33m and is operated by Amtrak.
Which bus companies service the Pittsfield to Chicago route?
What is the earliest and latest departure time for the bus from Pittsfield to Chicago?
The earliest bus departs from Pittsfield to Chicago at 08:20. And the latest bus departs at 17:40.
What are the CO₂ emissions for the bus trip from Pittsfield to Chicago?
A bus trip from Pittsfield to Chicago produces an estimated 30 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
What is the best bus company from Pittsfield to Chicago?
According to Busbud customers, the highest-rated bus company on this route is Amtrak, with an average rating of 4.1 out of 5 stars based on 5752 reviews.
Which bus company has the best Wi-Fi from Pittsfield to Chicago?
Based on reviews on Busbud, the bus company Amtrak has the best Wi-Fi rating with a score of 3.6.
Which bus company offers the most punctual service from Pittsfield to Chicago?
According to Busbud traveller reviews, the most punctual bus company on this route is Amtrak, with a punctuality rating of 3.8 out of 5 stars.
Which bus company has the cleanest buses from Pittsfield to Chicago?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is Amtrak, with a cleanliness rating of 4.5 out of 5 stars.
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 05 Feb 2026 with a price of R 1 944To 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.
You can expect to pay from R 1 944 to R 2 019 for a bus ticket from Pittsfield to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 1 944, which is on 2026-02-05.
What's the cheapest way to go from Pittsfield to Chicago?
The Bus is the cheapest travel choice for this destination
