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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 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
    6h 22m
    $96–438

  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 Poughkeepsietrain train
    6h 45m
    $72–318

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    18h 43m
    $160–340

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from TransCenter to Metro North Stationbus bus Wpp
    25h 3m
    $106–270

  5. Drive 812.5 mi

    1. Drive from Chicago to Poughkeepsiecar car 812.5 mi
    13h 34m
    $149–215

  6. 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
    7h 2m
    $140–788

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    7h 34m
    $120–638

  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)plane plane ORD - HPN
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    8h 33m
    $116–498

Chicago to Poughkeepsie by train (Amtrak)

Calendar7Weekly Trains
Duration18h 43mAverage Duration
Ticket$160Cheapest 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 $160–340 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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