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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 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 Peekskilltrain train
    5h 35m
    $146–730

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

    cheapest
    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 Peekskilltrain train
    6h 11m
    $84–342

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    20h
    $295–591

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    2. Take the bus from White Plains Bus Terminal Lane E to Nelson Ave @ Main Stbus bus 14 / ...
    27h 24m
    $150–245

  5. Drive 805 mi

    1. Drive from Chicago to Peekskillcar car 805 mi
    13h 25m
    $147–213

  6. 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 Peekskilltrain train
    5h 56m
    $106–290

  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)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    6h 58m
    $130–356

  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)plane plane ORD - HPN
    2. Take the train from White Plains to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Peekskilltrain train
    7h 48m
    $114–500

Chicago to Peekskill by train (Amtrak)

Calendar7Weekly Trains
Duration20hAverage Duration
Ticket$295Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Peekskill.ExpandLaunch map view
  • Distance: 777.3 mi
  • Duration: 5h 35m

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 $280–600 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 27h 24m.

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