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How to get fromSudbury to Chicagoby plane, train (Amtrak), bus (Flixbus), car, bus, or train

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There are 10 ways to get from Sudbury to Chicago by plane, train (Amtrak), bus (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
    5h 2m
    $119–451

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

    cheapest
    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
    7h 39m
    $115–456

  3. Train (Amtrak)

    1. Take the train from Framingham Amtrak to Chicago Union Stationtrain train Lake Shore Limited
    22h 2m
    $340–735

  4. Bus

    1. Take the bus from Newton, MA to Manhattan, NYbus bus Cambridge
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 5m
    $218–335

  5. Drive 966.4 mi

    1. Drive from Sudbury to Chicagocar car 966.4 mi
    16h 36m
    $177–255

  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)plane plane BOS - ORD
    5h 27m
    $634–1,041

  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
    7h 4m
    $130–526

  8. 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
    7h 33m
    $120–457

  9. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Framingham Amtrak to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 56m
    $136–508

  10. Fly Boston Logan Airport 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
    7h 31m
    $711–2,010

Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) flights

Calendar46Weekly Planes
Duration2h 49mAverage Duration
Ticket$84Cheapest Price
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Questions & Answers

Map of how to get from Sudbury to Chicago.ExpandLaunch map view
  • Distance: 897.5 mi
  • Duration: 5h 2m

What companies run services between Sudbury, 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 Framingham Amtrak to Chicago Union Station once daily. Tickets cost $310–700 and the journey takes 21h 47m.

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