Cheap buses leaving Tuesday
One passenger / one way
- This trip is recommended because it is the: CheapestDeparture time: June 24 atDeparture city: PittsfieldDeparture location: Pittsfield (Joseph Scelsi Intermodal)Arrival time: June 25 atDestination city: ChicagoDestination location: Chicago 95Th & Dan RyanOperated by: Greyhound Lines, Inc.
Vehicle: BusDuration: - This trip is recommended because it is the: FastestDeparture time: June 24 atDeparture city: PittsfieldDeparture location: Pittsfield (Joseph Scelsi Intermodal)Arrival time: June 25 atDestination city: ChicagoDestination location: Downtown Greyhound StationOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
- Departure time: June 24 atDeparture city: PittsfieldDeparture location: Pittsfield (Joseph Scelsi Intermodal)Arrival time: June 25 atDestination city: ChicagoDestination location: Downtown Greyhound StationOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
- Departure time: June 24 atDeparture city: PittsfieldDeparture location: Pittsfield (Joseph Scelsi Intermodal)Arrival time: June 25 atDestination city: ChicagoDestination location: 537-517 W. Jackson BlvdOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
- Departure time: June 24 atDeparture city: PittsfieldDeparture location: Pittsfield (Joseph Scelsi Intermodal)Arrival time: June 26 atDestination city: ChicagoDestination location: 537-517 W. Jackson BlvdOperated by: Greyhound Lines, Inc.Vehicle: BusDuration:
Last refresh of the prices: Last Tuesday at 12:46 AM EDT.
Prices and availability are subject to change.
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Compare 2 ways to go from Pittsfield to Chicago
Busbud recommends taking the train from Pittsfield to ChicagoAmong the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 18 hours 30 minutes, and with fares starting at just US$139, it presents an excellent value for a comfortable ride.
Bus Pittsfield to Chicago: Trip Overview
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Pittsfield to Chicago Bus
With Busbud, comparing and booking tickets for a bus from Pittsfield to Chicago is a breeze. Browse through an extensive selection of bus fares and bus schedules to find the best deals.
We make it our job to connect you with the most dependable bus companies that cover bus service from Pittsfield to Chicago.
From cheap bus tickets to more luxurious buses travelling from Pittsfield to Chicago, we offer a wide range of bus services to best suit your needs depending on how much your budget is.
Where are the popular stops in Pittsfield and Chicago?
Frequently asked questions on the trip Pittsfield - Chicago
How far is Pittsfield from Chicago?
The distance covered from Pittsfield to Chicago is 1186 km (736 miles).
What are the departure and arrival locations for buses traveling from Pittsfield to Chicago?
Buses traveling this route start their trip at Joseph Scelsi Intermodal Transportation Center, in Pittsfield, and end it at Downtown Greyhound Station, in Chicago.
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 Jun 24, 2025 with a price of US$168To 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 US$168 to US$707 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 US$168 which is on 2025-06-24.
About Bus Travel
Bus Travel Tips
Meet and talk to locals at the bus stations while travelling from Pittsfield to Chicago.There is no better way to get inside travel information while exploring a new city than to go straight to its people.
From miles long of beauteous natural landscapes to impressive man-crafted sights, you’re bound to be in for a visual treat on your bus trip from Pittsfield to Chicago.
Taking the bus creates the smallest carbon footprint compared to other modes of transport. Not to mention that buses will allow you to discover scenic gems from Pittsfield to Chicago that are otherwise impossible to come by with a plane.
Make a music playlist for your bus ride from Pittsfield to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!
One of the longest bus route in the world goes all the way from Ontario to Alberta in Canada (with the same bus). This trip is 3,435 km or 2,135 miles long and the price is a bit under $100.
The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.
What's the cheapest way to go from Pittsfield to Chicago?
The bus is the cheapest travel choice for this destinationTop travelled bus routes
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