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How to get fromChicago to Peekskillby plane, train, train (Amtrak), bus (Flixbus) or car

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There are 8 ways to get from Chicago to Peekskill 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 O'Hare International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    2. Take the train from 125th Street - Harlem to Peekskilltrain
    5h 47m
    $70–290

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak StationtrainLake Shore Limited
    20h 1m
    $91–283

  3. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from White Plains Bus Terminal Lane E to Nelson Ave @ Main Stbus0014 / ...
    24h 53m
    $119–232

  4. Drive 805 mi

    1. Drive from Chicago to Peekskillcar805 mi
    13h 17m
    $147–213

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

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    2. Take the train from 125th Street - Harlem to Peekskilltrain
    5h 34m
    $90–450

  6. 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)planeORD - JFK
    2. Take the train from Grand Central Terminal to Peekskilltrain
    6h 7m
    $828–1,142

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)planeORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain
    7h 3m
    $114–346

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)planeORD - HPN
    2. Take the train from White Plains to 125th Street - Harlemtrain
    3. Take the train from 125th Street - Harlem to Peekskilltrain
    7h 41m
    $494–940

Chicago to Peekskill by train (Amtrak)

Calendar7Weekly Trains
Duration20h 1mAverage Duration
Ticket$91Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $80–280 and the journey takes 19h 23m. Alternatively, you can take a bus from Chicago Bus Station to Nelson Ave @ Main St via New York Midtown, White Plains Bus Station, and White Plains Bus Terminal Lane E in around 24h 53m.

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