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

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There are 9 ways to get from South Boston to Chicago by ferry, 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. Ferry to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the ferry from Seaport to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    4h 47m
    $91–465

  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
    5h 46m
    $72–360

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 22m
    $250–600

  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
    $168–274

  5. Drive  980.9 mi

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

  6. Ferry to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the ferry from Seaport to Logan Airport Ferry Terminalferry ferry
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 5m
    $606–915

  7. 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 11m
    $130–667

  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 39m
    $105–517

  9. 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 39m
    $92–440

South Boston to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$250Cheapest Price
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Comparing Your Travel Options

Map of how to get from South Boston to Chicago.ExpandLaunch map view
  • Distance: 870.3 mi
  • Duration: 4h 47m

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

Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 22h 22m. Alternatively, you can take a bus from Boston to Chicago Bus Station via Newark Penn Station in around 26h.

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