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

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There are 10 ways to get from Wayland to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus

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 O'Hare International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 35m
    $141–357

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

    cheapest
    1. Take the train from Boston to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 17m
    $86–914

  3. Train (Amtrak)

    1. Take the train from Framingham Amtrak to Chicago Union Stationtrain train Lake Shore Limited
    22h 1m
    $277–2,132

  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
    $144–288

  5. Drive 968.3 mi

    1. Drive from Wayland to Chicagocar car 968.3 mi
    16h 32m
    $177–256

  6. Fly Boston Logan Airport to Chicago Midway International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 19m
    $116–487

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

    1. Take the train from Boston to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 54m
    $106–1,014

  8. 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 14m
    $153–671

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

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 35m
    $123–491

  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 20m
    $313–752

Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD) flights

Calendar119Weekly Planes
Duration3h 19mAverage Duration
Ticket$65Cheapest Price
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Questions & Answers

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

American Airlines, JetBlue Airways, and two other airlines fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Framingham Amtrak to Chicago Union Station once daily. Tickets cost $250–2,100 and the journey takes 21h 47m.

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