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How to get fromBoston to Chicago Loopby plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus or train

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There are 10 ways to get from Boston to Chicago Loop 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 Boston Logan Airport to Chicago O'Hare International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)planeBOS - ORD
    4h 53m
    $98–342

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

    cheapest
    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    6h 14m
    $59–864

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    22h 22m
    $150–700

  4. Bus

    1. Take the bus from Boston to Newark Penn StationbusGreyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus StationbusFlixBus N2640
    25h 44m
    $140–285

  5. Drive 981.7 mi

    1. Drive from Boston to Chicago Loopcar981.7 mi
    16h 40m
    $180–259

  6. Fly Boston Logan Airport to Chicago Midway International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    4h 43m
    $93–522

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    5h 19m
    $126–678

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)planeMHT - ORD
    5h 40m
    $96–468

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

    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    5h 59m
    $84–994

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

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    6h 46m
    $266–747

Boston to Chicago Loop by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$150Cheapest Price
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Questions & Answers

What companies run services between Boston, MA, USA and Chicago Loop, 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 $150–700 and the journey takes 22h 22m.

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