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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 O'Hare International Airport

    best
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 34m
    $76–288

  2. Train (Amtrak)

    cheapest
    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union StationtrainLake Shore Limited
    18h 2m
    $65–290

  3. Drive 812.2 mi

    1. Drive from Poughkeepsie to Chicagocar812.2 mi
    13h 24m
    $149–215

  4. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 23m
    $96–438

  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
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    6h 42m
    $131–688

  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
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    7h 12m
    $100–517

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

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    8h 39m
    $500–948

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

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    9h
    $194–638

Poughkeepsie to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 2mAverage Duration
Ticket$65Cheapest 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 $65–290 and the journey takes 18h 2m.

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