Rome2Rio

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

Find Transport to Wellesley

See all options

There are 9 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 32m
    $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
    7h 57m
    $66–339

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 24m
    $284–612

  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 41m
    $158–278

  5. Drive 968 mi

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

  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
    $164–432

  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 23m
    $124–631

  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 26m
    $92–479

  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 2m
    $90–441

Chicago to Wellesley by train (Amtrak)

Calendar7Weekly Trains
Duration22h 24mAverage Duration
Ticket$284Cheapest Price
See schedules

Questions & Answers

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 $280–650 and the journey takes 21h 28m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Trips from Chicago

Trips to Wellesley

Popular routes