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How to get fromWayland to Chicagoby plane, train (Amtrak), bus (Flixbus), car, bus or train

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There are 10 ways to get from Wayland to Chicago 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 12m
    $121–527

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

    cheapest
    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    7h 14m
    $86–944

  3. Train (Amtrak)

    1. Take the train from Framingham Amtrak to Chicago Union StationtrainLake Shore Limited
    22h
    $116–321

  4. Bus

    1. Take the bus from Newton, MA to Manhattan, NYbusCambridge
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 30m
    $149–278

  5. Drive 968.3 mi

    1. Drive from Wayland to Chicagocar968.3 mi
    16h 24m
    $177–256

  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
    5h 29m
    $126–347

  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
    7h 3m
    $153–732

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

    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    6h 52m
    $111–1,074

  9. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)planeMHT - ORD
    7h 31m
    $123–522

  10. 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 Chicago Union Stationtrain
    7h 19m
    $294–752

Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) flights

Calendar35Weekly Planes
Duration3h 29mAverage Duration
Ticket$90Cheapest Price
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Questions & Answers

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Framingham Amtrak to Chicago Union Station once daily. Tickets cost $90–290 and the journey takes 21h 47m.

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