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How to get fromPoughkeepsie to Chicago Union Stationby train, plane, train (Amtrak), bus (Flixbus), or car

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There are 8 ways to get from Poughkeepsie to Chicago Union Station 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 18m
    $223–691

  2. Train to Albany County Airport, fly to Chicago Midway International Airport

    cheapest
    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 42m
    $121–763

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 2m
    $230–550

  4. Bus

    1. Take the bus from Newburgh ShortLine Transportation Center to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 8m
    $142–246

  5. Drive  812.7 mi

    1. Drive from Poughkeepsie to Chicago Union Stationcar car 812.7 mi
    13h 34m
    $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 34m
    $153–591

  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 37m
    $162–926

  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 38m
    $131–600

Poughkeepsie to Chicago Union Station by train (Amtrak)

Calendar7Weekly Trains
Duration18h 2mAverage Duration
Ticket$230Cheapest Price
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Questions & Answers

Map of how to get from Poughkeepsie to Chicago Union Station.ExpandLaunch map view
  • Distance: 810.5 mi
  • Duration: 6h 18m

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $230–550 and the journey takes 18h 2m. Alternatively, you can take a train from Poughkeepsie to Chicago Union Station via Beacon, Beacon Station, Newburgh ShortLine Transportation Center, Port Authority Bus Terminal, New York Midtown, and Chicago Bus Station in around 22h 8m.

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