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How to get fromPittsfield to Wisconsinby train, plane, train (Amtrak), bus (Flixbus, Greyhound), car or bus

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There are 9 ways to get from Pittsfield to Wisconsin by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Train, train to Laguardia Airport, fly to General Mitchell International Airport

    best
    1. Take the train from Pittsfield Amtrak Station to Croton-Harmon Amtrak Stationtrain
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain
    3. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    9h 7m
    $205–590

  2. Train to Bradley International Airport, fly to Chicago Midway International Airport, train

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    3. Take the train from Chicago OTC to Kenoshatrain
    10h 18m
    $112–723

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union StationtrainLake Shore Limited
    2. Take the train from Chicago Union Station to MilwaukeetrainHiawatha Service / ...
    20h 59m
    $213–342

  4. Bus

    1. Take the bus from Pittsfield to Port Authority Bus Terminalbus
    2. Take the bus from New York Midtown to Chicago Bus Stationbus
    3. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus
    28h 21m
    $135–365

  5. Drive 939.3 mi

    1. Drive from Pittsfield to Milwaukeecar939.3 mi
    16h 17m
    $172–248

  6. Train, train to Laguardia Airport, fly to Dane County Regional Airport-Truax Field

    1. Take the train from Pittsfield Amtrak Station to Croton-Harmon Amtrak Stationtrain
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain
    3. Fly from Laguardia Airport (LGA) to Dane County Regional Airport-Truax Field (MSN)planeLGA - MSN
    9h 35m
    $166–811

  7. Bus to Albany County Airport, fly to Chicago Midway International Airport, train

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    3. Take the train from Chicago OTC to Kenoshatrain
    9h 4m
    $121–633

  8. Bus to Albany County Airport, fly to Chicago O'Hare International Airport, train

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)planeALB - ORD
    3. Take the train from Clybourn to Kenoshatrain
    9h 31m

  9. Train to Bradley International Airport, fly to Chicago O'Hare International Airport, train

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)planeBDL - ORD
    3. Take the train from Clybourn to Kenoshatrain
    10h 37m

Pittsfield to Wisconsin by train (Amtrak)

Calendar7Weekly Trains
Duration20h 59mAverage Duration
Ticket$213Cheapest Price
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Questions & Answers

What companies run services between Pittsfield, MA, USA and Wisconsin, USA?

You can take a train from Pittsfield Amtrak Station to Milwaukee via Chicago Union Station in around 20h 59m. Alternatively, you can take a bus from Pittsfield to Milwaukee Intermodal Station via Port Authority Bus Terminal, New York Midtown, and Chicago Bus Station in around 28h 21m.

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