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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)plane plane BOS - MDW
    5h 10m
    $121–537

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

    cheapest
    1. Take the train from Back Bay to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 58m
    $79–318

  3. Train (Amtrak)

    1. Take the train from Framingham Amtrak to Chicago Union Stationtrain train Lake Shore Limited
    22h 1m
    $297–632

  4. Bus

    1. Take the bus from Newton, MA to Manhattan, NYbus bus Cambridge
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 30m
    $183–298

  5. Drive 968.3 mi

    1. Drive from Wayland to Chicagocar car 968.3 mi
    16h 33m
    $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)plane plane BOS - ORD
    5h 32m
    $181–447

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

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 4m
    $157–759

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

    1. Take the train from Back Bay to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 26m
    $114–498

  9. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Framingham Amtrak to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 1m
    $152–875

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

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 29m
    $204–946

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

Calendar55Weekly Planes
Duration3h 6mAverage Duration
Ticket$94Cheapest 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) every 4 hours. Alternatively, Amtrak operates a train from Framingham Amtrak to Chicago Union Station once daily. Tickets cost $270–600 and the journey takes 21h 47m.

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