Bus Tickets from Pittsfield to Chicago

Next departures

Next departures for Pittsfield to Chicago on November 15
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Greyhound Lines, Inc.
Pittsfield (Joseph Scelsi Intermodal)
Downtown Greyhound StationCheapest
Amtrak
Joseph Scelsi Intermodal Transportation Center
Chicago (Union Station), ILFastest
Greyhound Lines, Inc. + FlixBus
Pittsfield (Joseph Scelsi Intermodal)
537-517 W. Jackson BlvdNo tags
Greyhound Lines, Inc.
Pittsfield (Joseph Scelsi Intermodal)
Chicago 95Th & Dan RyanNo tags

Last refresh of the prices: Last Wednesday at 6:40 PM EST.

Compare 2 ways to go from Pittsfield to Chicago

We recommend taking the bus

Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 5 hours 45 minutes and with fares starting at just $175, it presents an excellent value for a comfortable ride.

6bus per day
1d 5hAverage Duration
736 milesDistance
30kgCO₂ emissions
Average Price$175 - $387Average Duration1d 5h
30kg CO₂e
Average Price$76 - $76Average Duration18h 30m
108kg CO₂e

Frequently asked questions about traveling from Pittsfield to Chicago by bus

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
11/13
$117
11/14
No data
Today
$117
11/16
No data
11/17
No data
11/18
No data
11/19
No data
11/20
No data
busbud logoThe cheapest trip from Pittsfield to Chicago was searched and found on Nov 13, 2025 with a price of $117

To 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.

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