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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 10 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 to Boston Logan Airport, fly to General Mitchell International Airport

    best
    1. Take the train from Pittsfield Amtrak Station to Bostontrain train
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    8h 50m
    $744–2,038

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

    cheapest
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    3. Take the train from Clybourn to Kenoshatrain train
    9h 28m
    $108–511

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    2. Take the train from Chicago Union Station to Milwaukeetrain train Hiawatha Service / ...
    20h 59m
    $524–810

  4. Bus

    1. Take the bus from Pittsfield to New Yorkbus bus
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    3. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus bus
    28h 20m
    $195–311

  5. Drive  938.6 mi

    1. Drive from Pittsfield to Milwaukeecar car 938.6 mi
    16h 26m
    $172–248

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

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    3. Take the train from Chicago OTC to Kenoshatrain train
    9h 5m
    $128–680

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

    1. Take the train from Pittsfield Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Take the train from Albany-Rensselaer Amtrak Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    4. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    9h 54m
    $222–1,040

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

    1. Take the train from Pittsfield Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Take the train from Albany-Rensselaer Amtrak Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    4. Fly from Laguardia Airport (LGA) to Dane County Regional Airport-Truax Field (MSN)plane plane LGA - MSN
    10h 19m
    $231–1,089

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    3. Take the train from Chicago OTC to Kenoshatrain train
    10h 7m
    $132–532

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

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    3. Take the train from Clybourn to Kenoshatrain train
    10h 32m
    $112–433

Pittsfield to Wisconsin by train (Amtrak)

Calendar7Weekly Trains
Duration20h 59mAverage Duration
Ticket$524Cheapest Price
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Comparing Your Travel Options

Map of how to get from Pittsfield to Wisconsin.ExpandLaunch map view
  • Distance: 1,018.4 mi
  • Duration: 8h 50m

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 New York, 7 Av/W 41 St, 7 Av/W 34 St, New York Midtown, and Chicago Bus Station in around 28h 20m.

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