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How to get fromChicago Midway Airport (MDW) to Poughkeepsieby plane, train, train (Amtrak), bus (Flixbus), or car

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There are 6 ways to get from Chicago Midway Airport (MDW) to Poughkeepsie by plane, train, 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. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    4h 37m
    $228–576

  2. Drive 813.3 mi

    cheapest
    1. Drive from Chicago Midway Airport (MDW) to Poughkeepsiecar car 813.3 mi
    13h 40m
    $149–215

  3. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    7h 4m
    $236–696

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    20h 30m
    $286–608

  5. Bus

    1. Take the bus from Chicago to New York Midtownbus bus FlixBus N2640
    2. Take the bus from TransCenter to Metro North Stationbus bus Wpp
    27h 20m
    $160–282

  6. Fly Chicago Midway International Airport to Albany County Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    5h 30m
    $161–883

Chicago Midway Airport (MDW) to Poughkeepsie by subway, bus, and train (Amtrak)

Calendar7Weekly Services
Duration20h 30mAverage Duration
Ticket$286Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Poughkeepsie.ExpandLaunch map view
  • Distance: 798.4 mi
  • Duration: 4h 37m

What companies run services between Chicago Midway Airport (MDW), USA and Poughkeepsie, NY, USA?

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 43m. Alternatively, you can take a bus from Midway Orange Line Station to Metro North Station via Ashland & 59th Street, 95th Red Line Station, Chicago, New York Midtown, White Plains Station, and TransCenter in around 27h 20m.

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