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How to get fromChicago to Wellesleyby plane, train, train (Amtrak), bus (Flixbus), car or bus

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There are 8 ways to get from Chicago to Wellesley by plane, train, train (Amtrak), bus (Flixbus), car, or bus

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 Chicago O'Hare International Airport to Boston Logan Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Back Bay to Wellesley Squaretrain train
    5h 45m
    $134–402

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to Back Baytrain train
    7h 44m
    $62–309

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 22m
    $92–295

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from New York Midtown to Bostonbus bus FlixBus 2610 / ...
    26h 38m
    $130–241

  5. Drive 968 mi

    1. Drive from Chicago to Wellesleycar car 968 mi
    16h 35m
    $177–256

  6. Fly Chicago Midway International Airport to Boston Logan Airport

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    5h 25m
    $124–622

  7. Fly Chicago Midway International Airport to Manchester Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    7h 21m
    $138–733

  8. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to Back Baytrain train
    7h 24m
    $86–429

Chicago to Wellesley by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$92Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Framingham Amtrak once daily. Tickets cost $90–290 and the journey takes 21h 28m. Alternatively, you can take a bus from Chicago Bus Station to Wellesley Square via New York Midtown, Boston, and South Station in around 26h 38m.

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