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

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

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

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

    best
    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
    8h 39m
    $118–577

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

    cheapest
    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 18m
    $90–381

  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
    $312–618

  4. Bus

    1. Take the bus from Pittsfield to Port Authority Bus Terminalbus 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
    24h 46m
    $175–333

  5. Drive 938.6 mi

    1. Drive from Pittsfield to Milwaukeecar car 938.6 mi
    16h 27m
    $172–248

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

    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 8m
    $108–498

  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 56m
    $201–980

  8. 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
    9h 50m
    $100–440

  9. 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 20m
    $202–981

Pittsfield to Wisconsin by train (Amtrak)

Calendar7Weekly Trains
Duration20h 59mAverage Duration
Ticket$312Cheapest Price
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Questions & Answers

Map of how to get from Pittsfield to Wisconsin.ExpandLaunch map view
  • Distance: 825.5 mi
  • Duration: 8h 39m

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 24h 46m.

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