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How to get fromPeekskill to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car, or bus

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There are 8 ways to get from Peekskill to Chicago by train, plane, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Peekskill to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 28m
    $217–681

  2. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Peekskill to 125th Street - Harlemtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 48m
    $125–590

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 1m
    $266–610

  4. Bus

    1. Take the bus from Nelson Ave @ Main St to White Plains Bus Terminal Lane Bbus bus 14 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 19m
    $126–219

  5. Drive 804.9 mi

    1. Drive from Peekskill to Chicagocar car 804.9 mi
    13h 24m
    $147–213

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Peekskill to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 49m
    $147–581

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Peekskill to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 16m
    $339–893

  8. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Peekskill to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 38m
    $160–900

Peekskill to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration20h 1mAverage Duration
Ticket$266Cheapest Price
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Questions & Answers

Map of how to get from Peekskill to Chicago.ExpandLaunch map view
  • Distance: 777.6 mi
  • Duration: 5h 28m

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

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $260–600 and the journey takes 18h 46m. Alternatively, you can take a bus from Nelson Ave @ Main St to Chicago Bus Station via White Plains Bus Terminal Lane B, White Plains Station, and New York Midtown in around 22h 19m.

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