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

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There are 6 ways to get from Boston Airport (BOS) to Chicago by plane, bus (Greyhound, Flixbus), train (Amtrak), car, 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 to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    3h 11m
    $86–403

  2. 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 N2641 / ...
    23h 22m
    $222–367

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 28m
    $339–709

  4. Drive 983.3 mi

    1. Drive from Boston Airport (BOS) to Chicagocar car 983.3 mi
    16h 51m
    $180–260

  5. Fly to Chicago O'Hare International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    3h 36m
    $621–892

  6. Fly 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
    5h 38m
    $688–3,300

Boston Airport (BOS) to Chicago by bus and foot

Calendar22Weekly Services
Duration23h 22mAverage Duration
Ticket$222Cheapest Price
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Questions & Answers

Map of how to get from Boston Airport (BOS) to Chicago.ExpandLaunch map view
  • Distance: 868.3 mi
  • Duration: 3h 11m

What companies run services between Boston Airport (BOS), USA and Chicago, IL, USA?

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Terminal C - Arrivals Level to Chicago Bus Station via South Station, Boston, and Newark Penn Station in around 23h 22m.

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