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

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

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 15m
    $131–394

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Back Bay to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    6h 28m
    $53–260

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 26m
    $100–700

  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
    26h 47m
    $127–224

  5. Drive 979.2 mi

    1. Drive from Boston, MA to Chicagocar car 979.2 mi
    16h 43m
    $179–259

  6. 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
    4h 59m
    $96–474

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

    1. Take the train from Back Bay to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 5m
    $73–370

  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
    6h 45m
    $116–580

  9. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 10m
    $86–410

  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
    $183–979

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

Calendar7Weekly Services
Duration22h 26mAverage Duration
Ticket$100Cheapest Price
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Questions & Answers

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

American Airlines, JetBlue Airways, and two other airlines fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $100–700 and the journey takes 22h 15m.

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