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

Find Transport to Boston, MA

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There are 9 ways to get from Chicago to Boston, MA by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. Fly Chicago Midway International Airport to Boston Logan Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    4h 29m
    $122–664

  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 Back Baytrain train
    6h 53m
    $64–321

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    22h 5m
    $250–600

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from New York, NY - W 42nd Street and 9th Avenue to Boston, MA - Dalton and Belvidere Streetbus bus
    25h 10m
    $178–389

  5. Drive 980.3 mi

    1. Drive from Chicago to Boston, MAcar car 980.3 mi
    16h 45m
    $179–259

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    4h 53m
    $152–414

  7. 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 Back Baytrain train
    6h 23m
    $94–481

  8. 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 33m
    $134–724

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

    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
    7h 11m
    $94–454

Chicago to Boston, MA by train and foot (Amtrak)

Calendar7Weekly Services
Duration22h 5mAverage Duration
Ticket$250Cheapest Price
See schedules

Questions & Answers

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $250–600 and the journey takes 21h 54m.

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