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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 Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    4h 54m
    $96–454

  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 24m
    $64–863

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    22h 26m
    $140–750

  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
    26h 47m
    $127–294

  5. Drive 979.2 mi

    1. Drive from Boston, MA to Chicagocar979.2 mi
    16h 35m
    $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)planeBOS - ORD
    5h 15m
    $111–324

  7. 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 52m
    $84–953

  8. 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
    6h 35m
    $117–590

  9. 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
    7h 2m
    $97–450

  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
    7h
    $293–734

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

Calendar7Weekly Services
Duration22h 26mAverage Duration
Ticket$140Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $140–750 and the journey takes 22h 15m.

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