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How to get fromGloucester to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car, or bus

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There are 9 ways to get from Gloucester to Chicago by train, plane, train (Amtrak), bus (Flixbus), car, or bus

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

  1. Train to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Gloucester to Chelseatrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 38m
    $93–431

  2. Train

    1. Take the train from Gloucester to North Stationtrain train Newburyport/Rockport Line
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 34m
    $339–714

  3. Bus (Flixbus)

    1. Take the bus from Boston to New York Midtownbus bus FlixBus 2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    24h 57m
    $179–325

  4. Drive 1,010.3 mi

    1. Drive from Gloucester to Chicagocar car 1,010.3 mi
    17h 36m
    $185–267

  5. Train to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Gloucester to Chelseatrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 3m
    $608–1,021

  6. Train, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the train from Gloucester to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 31m
    $113–504

  7. Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Gloucester to North Stationtrain train
    2. Take the train from Ruggles to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 3m
    $95–424

  8. Train, bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Gloucester to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    8h 6m
    $98–434

  9. Train to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the train from Gloucester to Chelseatrain train
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 7m
    $685–1,990

Gloucester to Chicago by train and subway

Calendar7Weekly Services
Duration24h 34mAverage Duration
Ticket$339Cheapest Price
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Questions & Answers

Map of how to get from Gloucester to Chicago.ExpandLaunch map view
  • Distance: 899.5 mi
  • Duration: 5h 38m

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

You can take a train from Gloucester to Chicago Union Station via North Station, North Station, Back Bay, and Boston in around 24h 34m. Alternatively, you can take a bus from Commuter Rail Station - Gloucester to Chicago Bus Station via Commuter Rail Station - Beverly, Beverly, Chelsea, Chelsea, South Station, Boston, and New York Midtown in around 24h 57m.

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