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How to get fromChicago to Wappingers Fallsby plane, train, train (Amtrak), bus (Flixbus), car, or bus

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There are 9 ways to get from Chicago to Wappingers Falls by plane, train, 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. 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 Poughkeepsietrain train
    7h 52m
    $176–593

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from TransCenter to Hoebowl Family Recreation Centerbus bus
    8h 10m
    $102–566

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    20h 10m
    $294–578

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from TransCenter to Hoebowl Family Recreation Centerbus bus Wpp
    21h 40m
    $141–239

  5. Drive 805.2 mi

    1. Drive from Chicago to Wappingers Fallscar car 805.2 mi
    13h 22m
    $147–213

  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 Poughkeepsietrain train
    8h 12m
    $226–693

  7. 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 Ny Moynihan Train Hall At Penn Station to Poughkeepsie Amtrak Stationtrain train
    8h 31m
    $198–1,485

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

    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
    8h 31m
    $164–920

  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 Ny Moynihan Train Hall At Penn Station to Poughkeepsie Amtrak Stationtrain train
    9h 36m
    $192–1,060

Chicago to Wappingers Falls by train and bus (Amtrak)

Calendar7Weekly Services
Duration20h 10mAverage Duration
Ticket$294Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Wappingers Falls.ExpandLaunch map view
  • Distance: 818.6 mi
  • Duration: 7h 52m

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

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $290–600 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Hoebowl Family Recreation Center via New York Midtown, White Plains Station, and TransCenter in around 21h 40m.

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