Bus Tickets from Pittsfield to Chicago

Previously seen trips

Next departures for Pittsfield to Chicago on November 21
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
GreyhoundBus
Pittsfield (Joseph Scelsi Intermodal)
537-517 W. Jackson BlvdNo tags
GreyhoundBus
Pittsfield (Joseph Scelsi Intermodal)
Chicago 95Th & Dan RyanNo tags
GreyhoundBus
Pittsfield (Joseph Scelsi Intermodal)
Chicago 95Th & Dan RyanNo tags
GreyhoundBus
Pittsfield (Joseph Scelsi Intermodal)
537-517 W. Jackson BlvdNo tags
GreyhoundBus
Pittsfield (Joseph Scelsi Intermodal)
Downtown Greyhound StationNo tags

Compare 2 ways to go from Pittsfield to Chicago

We recommend taking the train

Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 18 hours 30 minutes and with fares starting at just $155, it presents an excellent value for a comfortable ride.

1train per day
18h 30mAverage Duration
736 milesDistance
108kgCO₂ emissions
Average Price$124 - $286Average Duration1d 5h
30kg CO₂e
Average Price$155 - $155Average 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
11/18
No data
11/19
$117
Today
$117
11/21
No data
11/22
No data
11/23
No data
11/24
No data
11/25
No data
busbud logoThe cheapest trip from Pittsfield to Chicago was searched and found on Nov 19, 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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