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

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There are 8 ways to get from Chicago to Wingdale by plane, train, bus, bus (Flixbus), or car

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 54m
    $100–507

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

    cheapest
    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 16m
    $70–317

  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
    $227–495

  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
    $126–221

  5. Drive 824.6 mi

    1. Drive from Chicago to Wingdalecar car 824.6 mi
    13h 52m
    $151–218

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Grand Central Terminal to Harlem Valley-Wingdaletrain train
    7h 43m
    $92–322

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

    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 47m
    $458–629

  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 18m
    $142–790

Chicago to Wingdale by train and bus

Calendar7Weekly Services
Duration20h 59mAverage Duration
Ticket$227Cheapest Price
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Questions & Answers

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.

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