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How to get fromBoston to Winnetkaby plane, train (Amtrak), bus (Flixbus), car, bus or train

Find Transport to Winnetka

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There are 9 ways to get from Boston to Winnetka 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 Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    5h 58m
    $90–488

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from South Station to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    7h 58m
    $64–844

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    23h 29m
    $152–667

  4. Bus (Flixbus)

    1. Take the bus from Boston to New York MidtownbusFlixBus 2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    28h 10m
    $134–267

  5. Drive 998.8 mi

    1. Drive from Boston to Winnetkacar998.8 mi
    17h 6m
    $183–264

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

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)planeBOS - ORD
    6h 7m
    $103–342

  7. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    6h 34m
    $128–634

  8. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from South Station to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    7h 34m
    $86–970

  9. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Glenview Amtrak Stationtrain
    7h 34m
    $266–750

Boston to Winnetka by train and foot (Amtrak)

Calendar7Weekly Services
Duration23h 29mAverage Duration
Ticket$152Cheapest Price
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Questions & Answers

What companies run services between Boston, MA, USA and Winnetka, IL, USA?

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $150–700 and the journey takes 22h 22m.

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