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

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There are 10 ways to get from Chicago to Wellesley 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 Chicago O'Hare International Airport to Boston Logan Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    5h 54m
    $194–572

  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 52m
    $78–379

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 22m
    $275–598

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to Bostonbus bus FlixBus 2610 / ...
    23h 29m
    $145–250

  5. Drive 967.3 mi

    1. Drive from Chicago to Wellesleycar car 967.3 mi
    16h 37m
    $177–255

  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 29m
    $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 20m
    $142–730

  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
    $104–519

  9. Fly Chicago O'Hare International Airport to Manchester Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    7h 59m
    $102–510

  10. Fly Chicago Midway International Airport to Bradley International Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Hartford Union Station to Worcester Union Stationbus bus
    3. Take the train from Worcester to Wellesley Squaretrain train
    8h 12m
    $130–697

Chicago to Wellesley by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$275Cheapest Price
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Questions & Answers

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

American Airlines, JetBlue Airways, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS) hourly. Alternatively, Amtrak operates a train from Chicago Union Station to Framingham Amtrak once daily. Tickets cost $270–600 and the journey takes 21h 28m.

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