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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 8 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
    6h 33m
    $223–591

  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 27m
    $101–566

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 30m
    $262–602

  4. Bus

    1. Take the bus from Newburgh ShortLine Transportation Center to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 6m
    $146–256

  5. Drive 804.7 mi

    1. Drive from Wappingers Falls to Chicagocar car 804.7 mi
    13h 21m
    $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
    6h 54m
    $153–691

  7. 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 2m
    $167–935

  8. 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
    7h 52m
    $133–770

Wappingers Falls to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration19h 30mAverage Duration
Ticket$262Cheapest Price
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Questions & Answers

Map of how to get from Wappingers Falls to Chicago.ExpandLaunch map view
  • Distance: 803.8 mi
  • Duration: 6h 33m

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 $260–600 and the journey takes 18h 2m. Alternatively, you can take a bus from Mesier Park Southbound to Chicago Bus Station via Beacon Station, Newburgh ShortLine Transportation Center, Port Authority Bus Terminal, and New York Midtown in around 22h 6m.

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