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How to get fromChicago to Pound Ridgeby plane, train (Amtrak), bus (Flixbus, Greyhound), car, train or bus

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There are 8 ways to get from Chicago to Pound Ridge by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, or bus

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 O'Hare International Airport to Westchester County Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    4h 22m
    $122–495

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

    cheapest
    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 Katonahtrain train
    6h 9m
    $106–361

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    19h 59m
    $184–340

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus Greyhound US0240
    24h 42m
    $119–194

  5. Drive 825.3 mi

    1. Drive from Chicago to Pound Ridgecar car 825.3 mi
    14h 3m
    $151–218

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    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 Katonahtrain train
    5h 51m
    $136–551

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Katonahtrain train
    6h 30m
    $768–1,093

  8. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Stamfordtrain train
    25h 3m
    $135–310

Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) flights

Calendar47Weekly Planes
Duration3h 8mAverage Duration
Ticket$79Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Pound Ridge, NY, USA?

American Airlines and Delta fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $130–280 and the journey takes 19h 23m.

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