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How to get fromChicago to Massachusettsby plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus or train

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There are 10 ways to get from Chicago to Massachusetts by plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus, 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 Chicago O'Hare International Airport to Boston Logan Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    4h 34m
    $116–368

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    6h 37m
    $58–311

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    22h 2m
    $85–370

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus FlixBus N2640
    2. Take the bus from Newark Penn Station to Bostonbus bus Greyhound US0235 / ...
    25h 30m
    $138–241

  5. Drive 981.1 mi

    1. Drive from Chicago to Bostoncar car 981.1 mi
    16h 49m
    $179–259

  6. Fly Chicago Midway International Airport to Boston Logan Airport

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    4h 14m
    $116–608

  7. Fly Chicago Midway International Airport to Bradley International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    5h 23m
    $106–798

  8. Fly Chicago O'Hare International Airport to Bradley International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    6h 1m
    $80–628

  9. Fly Chicago Midway International Airport to Manchester Airport, bus

    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
    6h 6m
    $126–675

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

    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 South Stationtrain train
    6h 17m
    $84–421

Chicago to Massachusetts by train (Amtrak)

Calendar7Weekly Trains
Duration22h 2mAverage Duration
Ticket$85Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Massachusetts, USA?

American Airlines, JetBlue Airways, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS) hourly. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $85–370 and the journey takes 22h 2m.

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