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

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There are 8 ways to get from Chicago to Poughkeepsie by plane, train, train (Amtrak), 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 O'Hare International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain
    6h 37m
    $76–298

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak StationtrainLake Shore Limited
    18h 43m
    $110–270

  3. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from TransCenter to Metro North StationbusWpp
    25h 3m
    $118–267

  4. Drive 812.5 mi

    1. Drive from Chicago to Poughkeepsiecar812.5 mi
    13h 26m
    $149–215

  5. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain
    6h 22m
    $86–408

  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)planeORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Poughkeepsie Amtrak Stationtrain
    7h 5m
    $118–365

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

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)planeMDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain
    7h 3m
    $140–738

  8. 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)planeORD - HPN
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain
    8h 34m
    $500–948

Chicago to Poughkeepsie by train (Amtrak)

Calendar7Weekly Trains
Duration18h 43mAverage Duration
Ticket$110Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $110–270 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Metro North Station via New York Midtown, White Plains Bus Station, and TransCenter in around 25h 3m.

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