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How to get fromPoughkeepsie to Chicagoby train, plane, train (Amtrak) or car

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There are 8 ways to get from Poughkeepsie to Chicago by train, plane, train (Amtrak), 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 29m
    $101–488

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

    cheapest
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 45m
    $71–318

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 2m
    $130–340

  4. Drive 812.2 mi

    1. Drive from Poughkeepsie to Chicagocar car 812.2 mi
    13h 32m
    $149–215

  5. 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
    6h 57m
    $121–638

  6. 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
    7h 27m
    $81–566

  7. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 41m
    $95–398

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

    1. Take the train from Poughkeepsie 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
    $233–703

Poughkeepsie to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 2mAverage Duration
Ticket$130Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $130–340 and the journey takes 18h 2m.

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