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

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There are 9 ways to get from Wappingers Falls to Chicago by train, plane, train (Amtrak), bus (Flixbus), car, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from New Hamburg to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 8m
    $102–498

  2. Bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Hoebowl Family Recreation Center to TransCenterbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 38m
    $61–346

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 30m
    $122–322

  4. Bus

    1. Take the bus from Hoebowl Family Recreation Center to TransCenterbus bus Wpp
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 24m
    $100–221

  5. Drive 804.7 mi

    1. Drive from Wappingers Falls to Chicagocar car 804.7 mi
    13h 20m
    $147–213

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from New Hamburg to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 23m
    $72–288

  7. Train to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 25m
    $118–645

  8. Train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Poughkeepsie Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 56m
    $83–557

  9. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from New Hamburg to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 39m
    $234–703

Wappingers Falls to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration19h 30mAverage Duration
Ticket$122Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $120–320 and the journey takes 18h 2m. Alternatively, you can take a bus from Hoebowl Family Recreation Center to Chicago Bus Station via TransCenter, White Plains Bus Station, and New York Midtown in around 25h 24m.

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