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

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There are 9 ways to get from Chicago to Wellesley by plane, train (Amtrak), bus (Flixbus, Greyhound), 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
    $124–622

  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 2m
    $64–289

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 31m
    $548–847

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus FlixBus N2640 / ...
    2. Take the bus from Newark Penn Station to Bostonbus bus Greyhound US0235 / ...
    27h 5m
    $189–293

  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
    $564–1,022

  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 30m
    $114–578

  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
    $88–429

  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 58m
    $78–378

Chicago to Wellesley by train (Amtrak)

Calendar7Weekly Trains
Duration22h 31mAverage Duration
Ticket$548Cheapest Price
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Comparing Your Travel Options

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) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Framingham Amtrak once daily. Tickets cost $500–850 and the journey takes 21h 28m.

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