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

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There are 10 ways to get from Massachusetts to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 Bradley International Airport to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    5h 5m
    $95–685

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

    cheapest
    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    5h 26m
    $65–535

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 22m
    $100–600

  4. Bus

    1. Take the bus from Boston to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2640
    25h 30m
    $126–255

  5. Drive 980.8 mi

    1. Drive from Boston to Chicagocar car 980.8 mi
    16h 45m
    $179–259

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

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 16m
    $114–367

  7. Fly Boston Logan Airport to Chicago Midway International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 1m
    $89–467

  8. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    5h 26m
    $115–626

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

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    5h 54m
    $73–391

  10. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 1m
    $306–722

Massachusetts to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$100Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $100–600 and the journey takes 22h 22m.

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