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

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There are 8 ways to get from Poughkeepsie to Chicago by train, plane, 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. 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
    $173–591

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

    cheapest
    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
    $116–490

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 2m
    $290–600

  4. Bus

    1. Take the bus from Newburgh ShortLine Transportation Center to 9th Ave & W 30th Stbus bus ShortLine Hudson
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 47m
    $154–283

  5. Drive 812.2 mi

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

  6. 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 33m
    $223–691

  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
    6h 35m
    $196–1,480

  8. 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 32m
    $121–713

Poughkeepsie to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 2mAverage Duration
Ticket$290Cheapest Price
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Questions & Answers

Map of how to get from Poughkeepsie to Chicago.ExpandLaunch map view
  • Distance: 809.8 mi
  • Duration: 6h 12m

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 $290–600 and the journey takes 18h 2m. Alternatively, you can take a train from Poughkeepsie to Chicago Bus Station via Beacon, Beacon Station, Newburgh ShortLine Transportation Center, 9th Ave & W 30th St, and New York Midtown in around 21h 47m.

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