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

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There are 9 ways to get from Poughkeepsie to Chicago by train, plane, train (Amtrak), bus, 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 12m

  2. Drive 812.2 mi

    cheapest
    1. Drive from Poughkeepsie to Chicagocar car 812.2 mi
    13h 33m
    $149–215

  3. Train (Amtrak)

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

  4. Bus

    1. Take the bus from Metro North Station to TransCenterbus bus Wpp
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 41m

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

    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 29m

  6. 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 37m

  7. 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 25m

  8. 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 30m

  9. 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
    8h 46m

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar60Weekly Planes
Duration3h 5mAverage Duration
Ticket$87Cheapest 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, and the journey takes 18h 2m. Alternatively, you can take a bus from Metro North Station to Chicago Bus Station via TransCenter, White Plains Bus Station, and New York Midtown in around 25h 41m.

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