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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 Midway International Airport to Boston Logan Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    5h 35m
    $114–522

  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
    8h
    $68–309

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 23m
    $290–628

  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 36m
    $160–265

  5. Drive 967.3 mi

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

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    5h 54m
    $614–1,022

  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 27m
    $112–579

  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 30m
    $84–389

  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
    8h
    $92–439

  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 to Worcesterbus bus
    3. Take the train from Worcester to Wellesley Squaretrain train
    8h 15m
    $120–599

Chicago to Wellesley by train (Amtrak)

Calendar7Weekly Trains
Duration22h 23mAverage Duration
Ticket$290Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Wellesley.ExpandLaunch map view
  • Distance: 892.7 mi
  • Duration: 5h 35m

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Framingham Amtrak once daily. Tickets cost $280–650 and the journey takes 21h 28m.

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