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

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There are 8 ways to get from Chicago to Peekskill by plane, train, train (Amtrak), bus (Flixbus), car, 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 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 24m
    $218–682

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, line 13 bus, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from N Broadway @ Main St to Tarrytown Railroad Stationbus bus
    3. Take the train from Tarrytown to Peekskilltrain train
    7h 38m
    $100–474

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    19h 48m
    $256–559

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from White Plains Bus Terminal Lane E to Nelson Ave @ Main Stbus bus 14 / ...
    21h 49m
    $130–207

  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 46m
    $148–582

  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 Peekskilltrain train
    5h 57m
    $338–893

  8. 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 48m
    $158–914

Chicago to Peekskill by train (Amtrak)

Calendar7Weekly Trains
Duration19h 48mAverage Duration
Ticket$256Cheapest 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 24m

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 $250–550 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 Station, and White Plains Bus Terminal Lane E in around 21h 49m.

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