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How to get fromMilwaukee to Gloucesterby plane, train, train (Amtrak), bus, or car

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There are 7 ways to get from Milwaukee to Gloucester by plane, train, train (Amtrak), bus, 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. Fly from General Mitchell International Airport, train

    best
    1. Fly from General Mitchell International Airport (MKE) to Boston Logan Airport (BOS)plane plane MKE - BOS
    2. Take the train from Chelsea to Gloucestertrain train
    6h 5m
    $658–1,918

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

    cheapest
    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    8h 4m
    $138–580

  3. Train

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Bostontrain train
    3. Take the train from North Station to Gloucestertrain train
    26h 34m
    $355–771

  4. Bus, train

    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 Midtown to Bostonbus bus
    4. Take the train from Chelsea to Gloucestertrain train
    27h 18m
    $189–341

  5. Drive 1,099.6 mi

    1. Drive from Milwaukee to Gloucestercar car 1,099.6 mi
    19h 14m
    $201–290

  6. Bus to Chicago O'Hare International Airport, fly, 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 Boston Logan Airport (BOS)plane plane ORD - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    7h 38m
    $644–1,057

  7. Bus to Dane County Regional Airport-Truax Field, fly, train

    1. Take the bus from Milwaukee, WI - Amtrak to Madison, WI-Lake St.bus bus
    2. Fly from Dane County Regional Airport-Truax Field (MSN) to Boston Logan Airport (BOS)plane plane MSN - BOS
    3. Take the train from Chelsea to Gloucestertrain train
    8h 26m
    $140–641

Milwaukee to Gloucester by train and subway

Calendar7Weekly Services
Duration26h 34mAverage Duration
Ticket$355Cheapest Price
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Questions & Answers

Map of how to get from Milwaukee to Gloucester.ExpandLaunch map view
  • Distance: 896 mi
  • Duration: 6h 5m

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

You can take a train from Milwaukee to Gloucester via Chicago Union Station, Boston, Back Bay, North Station, and North Station in around 26h 34m.

Airlines
Train operators
Bus operators

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