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

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There are 9 ways to get from Chicago 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 Chicago O'Hare International Airport to Boston Logan Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Chelsea to Gloucestertrain train
    6h 34m
    $608–1,021

  2. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to Rugglestrain train
    3. Take the train from North Station to Gloucestertrain train
    8h 31m
    $94–406

  3. Train

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the train from North Station to Gloucestertrain train Newburyport/Rockport Line
    24h 5m
    $338–684

  4. Bus, train via Brook Park

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Bostonbus bus
    3. Take the train from Chelsea to Gloucestertrain train
    24h 24m
    $159–316

  5. Drive 1,010.7 mi

    1. Drive from Chicago to Gloucestercar car 1,010.7 mi
    17h 35m
    $185–267

  6. Fly Chicago Midway International Airport to Boston Logan Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Chelsea to Gloucestertrain train
    6h 17m
    $108–521

  7. Fly Chicago Midway International Airport to Manchester Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the train from North Station to Gloucestertrain train
    8h 26m
    $118–585

  8. Fly Chicago O'Hare International Airport to Manchester Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the train from North Station to Gloucestertrain train
    9h
    $102–455

  9. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the train from Chelsea to Gloucestertrain train
    24h 38m
    $187–318

Chicago to Gloucester by train and subway

Calendar7Weekly Services
Duration24h 5mAverage Duration
Ticket$338Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Gloucester.ExpandLaunch map view
  • Distance: 912.8 mi
  • Duration: 6h 34m

What companies run services between Chicago, IL, USA and Gloucester, MA, USA?

You can take a train from Chicago Union Station to Gloucester via Boston, Back Bay, North Station, and North Station in around 24h 5m.

Airlines
Train operators
Bus operators

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