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

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There are 11 ways to get from Milwaukee to Pittsfield by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), 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. Bus to Chicago O'Hare International Airport, fly to Albany County Airport, bus

    best
    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
    7h 57m
    $147–658

  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 5m
    $139–543

  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
    $231–549

  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 New York to Pittsfieldbus bus
    28h 23m
    $184–310

  5. Drive  940.1 mi

    1. Drive from Milwaukee to Pittsfieldcar car 940.1 mi
    16h 25m
    $172–248

  6. 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 7m
    $696–2,001

  7. 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 24m
    $190–918

  8. 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 31m
    $172–871

  9. 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 26m
    $618–940

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

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    3. Take the train from Springfield to Pittsfield Amtrak Stationtrain train
    9h 42m
    $149–746

  11. Bus to Chicago O'Hare International Airport, fly to Syracuse Hancock International Airport, train

    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 Syracuse Hancock International Airport (SYR)plane plane ORD - SYR
    3. Take the train from Syracuse Regional Transportation Center to Pittsfield Amtrak Stationtrain train
    11h 41m
    $206–888

Milwaukee to Pittsfield by train (Amtrak)

Calendar7Weekly Trains
Duration20h 29mAverage Duration
Ticket$231Cheapest Price
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Comparing Your Travel Options

Map of how to get from Milwaukee to Pittsfield.ExpandLaunch map view
  • Distance: 850.1 mi
  • Duration: 7h 57m

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, 8 Av/W 31 St, 8 Av/W 41 St, and New York in around 28h 23m.

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