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Chicago to Pittsfield, MA, USA - Transfer & Transportation Guides

Find transfer & transportation guides from Chicago to Pittsfield, MA, USA. How to get from Chicago to Pittsfield, MA, USA by Flight, Bus, Train.

You can get to Pittsfield, MA, USA from Chicago by verhicle types below

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Transfer solutions

You have 9 options transfer to Pittsfield, MA, USA from Chicago below

1. Fly Chicago Midway to Albany + train
Subway ( 23 min. )

Take a subway from Adams/Wabash to Midway.

Open Map More details & check price at Chicago Transit (CTA)
Walk ( 7 min. )

Take a foot from Midway to Chicago Midway.

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Plane ( 1 hr. 45 min. )

Take a flight from Chicago Midway to Albany.

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Bus ( 40 min. )

Take a bus from Albany International Airport to AMTRAK Station Rensselaer.

Open Map More details & check price at Vermont Translines
Train ( 1 hr. 3 min. )

Take a train from Albany-Rensselaer Amtrak Station to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 6 hr. 58 min.
Distance 1263 km.
Cost 414 USD
2. Fly Chicago O'Hare to Albany + train
Subway ( 42 min. )

Take a subway from Jackson-Blue to O'Hare.

Open Map More details & check price at Chicago Transit (CTA)
Plane ( 1 hr. 54 min. )

Take a flight from Chicago O'Hare to Albany.

Open Map Check Flights
Bus ( 40 min. )

Take a bus from Albany International Airport to AMTRAK Station Rensselaer.

Open Map More details & check price at Vermont Translines
Train ( 1 hr. 3 min. )

Take a train from Albany-Rensselaer Amtrak Station to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 7 hr. 19 min.
Distance 1284 km.
Cost 234 USD
3. Fly Chicago Midway to Hartford + train
Subway ( 23 min. )

Take a subway from Adams/Wabash to Midway.

Open Map More details & check price at Chicago Transit (CTA)
Walk ( 7 min. )

Take a foot from Midway to Chicago Midway.

Open Map
Plane ( 1 hr. 55 min. )

Take a flight from Chicago Midway to Hartford.

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Bus ( 16 min. )

Take a bus from Bradley Intl Airport and Terminal A to S Main St and Amtrak Windsor Lock.

Open Map More details & check price at CT Transit
Train ( 25 min. )

Take a train from Windsor Locks to Springfield.

Open Map More details & check price at Amtrak
Train ( 1 hr. 16 min. )

Take a train from Springfield to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 8 hr. 22 min.
Distance 1380 km.
Cost 340 USD
4. Fly Chicago O'Hare to Hartford + train
Subway ( 42 min. )

Take a subway from Jackson-Blue to O'Hare.

Open Map More details & check price at Chicago Transit (CTA)
Plane ( 2 hr. 1 min. )

Take a flight from Chicago O'Hare to Hartford.

Open Map Check Flights
Bus ( 16 min. )

Take a bus from Bradley Intl Airport and Terminal A to S Main St and Amtrak Windsor Lock.

Open Map More details & check price at CT Transit
Train ( 25 min. )

Take a train from Windsor Locks to Springfield.

Open Map More details & check price at Amtrak
Train ( 1 hr. 16 min. )

Take a train from Springfield to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 8 hr. 40 min.
Distance 1403 km.
Cost 210 USD
5. Fly Chicago O'Hare to Syracuse + train
Subway ( 42 min. )

Take a subway from Jackson-Blue to O'Hare.

Open Map More details & check price at Chicago Transit (CTA)
Plane ( 1 hr. 42 min. )

Take a flight from Chicago O'Hare to Syracuse.

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Bus ( 15 min. )

Take a bus from Syracuse, NY - Airport to Syracuse, NY.

Open Map More details & check price at Trailways New York
Train ( 4 hr. 45 min. )

Take a train from Syracuse Regional Transportation Center to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 10 hr. 24 min.
Distance 1331 km.
Cost 238 USD
6. Fly Chicago Midway to Manchester + bus + train
Subway ( 23 min. )

Take a subway from Adams/Wabash to Midway.

Open Map More details & check price at Chicago Transit (CTA)
Walk ( 7 min. )

Take a foot from Midway to Chicago Midway.

Open Map
Plane ( 2 hr. )

Take a flight from Chicago Midway to Manchester.

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Taxi ( 12 min. )

Take a taxi from Manchester to North Londonderry, NH - exit 5.

Open Map More details & check price at Manchester Taxi
Bus ( 1 hr. )

Take a bus from North Londonderry, NH - exit 5 to Boston South Buses.

Open Map More details & check price at Boston Express
Train ( 3 hr. 49 min. )

Take a train from Boston to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 10 hr. 16 min.
Distance 1691 km.
Cost 488 USD
7. Train
Train ( 17 hr. 38 min. )

Take a train from Chicago Union Station to Pittsfield Amtrak Station.

Open Map More details & check price at Amtrak
Duration 17 hr. 38 min.
Distance 1391 km.
Cost 110 USD
8. Bus
Bus ( 13 hr. )

Take a bus from Chicago to New York, NY - 3 Allen St.

Open Map More details & check price at Wanda Coach
Bus ( 3 hr. 15 min. )

Take a bus from Chinatown-152 East Broadway to Albany, NY.

Open Map More details & check price at Fox Bus
Bus ( 11 min. )

Take a bus from Central Ave & Lexington Ave to Madison Ave & Green Street.

Open Map More details & check price at Capital District Transportation (CDTA)
Bus ( 1 hr. )

Take a bus from Albany to Pittsfield.

Open Map More details & check price at Greyhound USA
Duration 19 hr. 33 min.
Distance 1578 km.
Cost 142 USD
9. Drive
Car ( 14 hr. 37 min. )

Drive a car from Chicago to Pittsfield.

Open Map
Duration 14 hr. 37 min.
Distance 1370 km.
Cost 84 USD

Find Hotels in Pittsfield, MA, USA

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About Chicago, IL, USA

Chicago ( (listen), locally also ), officially the City of Chicago, is the most populous city in the U.S. state of Illinois, and the third-most-populous city in the United States. With an estimated population of 2,693,976 in 2019, it is also the most... Learn more

About Pittsfield, MA, USA

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References