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

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There are 10 ways to get from Wellesley 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 35m
    $99–472

  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
    7h 21m
    $74–369

  3. Train (Amtrak)

    1. Take the train from Framingham Amtrak to Chicago Union Stationtrain train Lake Shore Limited
    23h 1m
    $241–607

  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 N2640 / ...
    26h 43m
    $182–276

  5. Drive  967.7 mi

    1. Drive from Wellesley to Chicagocar car 967.7 mi
    16h 37m
    $177–256

  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 53m
    $614–922

  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
    6h 52m
    $133–676

  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 14m
    $94–449

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

    1. Take the train from Wellesley Square to Worcestertrain train
    2. Take the bus from Worcester to Hartfordbus bus
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 59m
    $101–472

  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
    8h 14m
    $684–1,981

Wellesley to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 1mAverage Duration
Ticket$241Cheapest Price
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Comparing Your Travel Options

Map of how to get from Wellesley to Chicago.ExpandLaunch map view
  • Distance: 887.1 mi
  • Duration: 5h 35m

What companies run services between Wellesley, 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 $240–600 and the journey takes 21h 47m.

Airlines
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Bus operators

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