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How to get fromChicago to Wingdaleby plane, train, bus, bus (Flixbus), car, or shuttle

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There are 9 ways to get from Chicago to Wingdale by plane, train, bus, bus (Flixbus), car, or shuttle

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 Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Harlem Valley-Wingdaletrain train
    6h 58m
    $222–690

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Harlem Valley-Wingdaletrain train
    7h 53m
    $100–480

  3. Train, bus

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Take the bus from Poughkeepsie Train Station to Cousins Cafebus bus E
    20h 59m
    $489–749

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from TransCenter to Metro North Stationbus bus Wpp
    3. Take the bus from Poughkeepsie Train Station to Cousins Cafebus bus E
    27h 19m
    $164–248

  5. Drive  824.6 mi

    1. Drive from Chicago to Wingdalecar car 824.6 mi
    13h 53m
    $151–218

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Harlem Valley-Wingdaletrain train
    7h 18m
    $152–590

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, shuttle, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    3. Take the train from Grand Central Terminal to Southeasttrain train
    8h 36m
    $178–842

  8. Fly Chicago Midway International Airport to Albany County Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    3. Take the bus from Poughkeepsie Train Station to Cousins Cafebus bus
    9h 20m
    $174–1,020

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Grand Central Terminal to Southeasttrain train
    9h 23m
    $200–1,019

Chicago to Wingdale by train and bus

Calendar7Weekly Services
Duration20h 59mAverage Duration
Ticket$489Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Wingdale.ExpandLaunch map view
  • Distance: 805.8 mi
  • Duration: 6h 58m

What companies run services between Chicago, IL, USA and Wingdale, NY, USA?

You can take a bus from Chicago Bus Station to Cousins Cafe via New York Midtown, White Plains Bus Station, TransCenter, and Poughkeepsie Train Station in around 27h 19m.

Airlines
Train operators
Bus operators

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