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How to get fromMilwaukee to Pittsfieldby plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car or train

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There are 10 ways to get from Milwaukee to Pittsfield by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, or train

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

  1. Fly General Mitchell International Airport to Albany County Airport, bus

    best
    1. Fly from General Mitchell International Airport (MKE) to Albany County Airport (ALB)plane plane MKE - ALB
    2. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    8h 47m
    $168–952

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

    cheapest
    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    3. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    9h 11m
    $132–821

  3. Train (Amtrak)

    1. Take the train from Milwaukee to Chicago Union Stationtrain train Hiawatha Service / ...
    2. Take the train from Chicago Union Station to Pittsfield Amtrak Stationtrain train Lake Shore Limited
    20h 29m
    $192–338

  4. Bus

    1. Take the bus from Milwaukee Intermodal Station to Chicago Bus Stationbus bus
    2. Take the bus from Chicago Bus Station to New York Midtownbus bus
    3. Take the bus from Port Authority Bus Terminal to Pittsfieldbus bus
    28h 56m
    $134–370

  5. Drive 940.7 mi

    1. Drive from Milwaukee to Pittsfieldcar car 940.7 mi
    16h 23m
    $172–248

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

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    3. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    8h 5m
    $136–540

  7. Fly General Mitchell International Airport to Boston Logan Airport, train

    1. Fly from General Mitchell International Airport (MKE) to Boston Logan Airport (BOS)plane plane MKE - BOS
    2. Take the train from Boston to Pittsfield Amtrak Stationtrain train
    9h 2m
    $314–869

  8. Fly General Mitchell International Airport to Laguardia Airport, train

    1. Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane plane MKE - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    9h 23m
    $245–756

  9. Train to Chicago Midway International Airport, fly to Albany County Airport, bus

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    3. Take the bus from Albany Bus Terminal, NY to Pittsfieldbus bus
    8h 29m
    $160–765

  10. Fly General Mitchell International Airport to Newark Liberty International Airport, train

    1. Fly from General Mitchell International Airport (MKE) to Newark Liberty International Airport (EWR)plane plane MKE - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Pittsfield Amtrak Stationtrain train
    9h 23m
    $282–778

Milwaukee to Pittsfield by train (Amtrak)

Calendar7Weekly Trains
Duration20h 29mAverage Duration
Ticket$192Cheapest Price
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Questions & Answers

What companies run services between Milwaukee, WI, USA and Pittsfield, MA, USA?

You can take a train from Milwaukee to Pittsfield Amtrak Station via Chicago Union Station in around 20h 29m. Alternatively, you can take a bus from Milwaukee Intermodal Station to Pittsfield via Chicago Bus Station, New York Midtown, and Port Authority Bus Terminal in around 28h 56m.

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