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

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There are 8 ways to get from South Boston 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 Boston Logan Airport 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
    $83–399

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

    cheapest
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    3h 37m
    $71–340

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 22m
    $330–700

  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 N2641 / ...
    22h 40m
    $160–285

  5. Drive 980.9 mi

    1. Drive from South Boston to Chicagocar car 980.9 mi
    16h 50m
    $179–259

  6. 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 6m
    $100–480

  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
    5h 44m
    $87–390

  8. 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
    5h 41m
    $85–410

South Boston to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$330Cheapest Price
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Questions & Answers

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

What companies run services between South Boston, MA, 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, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $330–700 and the journey takes 22h 22m.

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