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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 9 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 O'Hare International Airport

    best
    1. Take the train from Peekskill to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 54m
    $71–290

  2. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union StationtrainLake Shore Limited
    20h 1m
    $127–321

  3. Bus

    1. Take the bus from Nelson Ave @ Main St to White Plains Bus Terminal Lane Bbus0014 / ...
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 19m
    $107–218

  4. Drive 804.9 mi

    1. Drive from Peekskill to Chicagocar804.9 mi
    13h 15m
    $147–213

  5. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Peekskill to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 41m
    $96–470

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

    1. Take the train from Peekskill to Grand Central Terminaltrain
    2. Take the bus from Bryant Park to Terminal Bbus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    6h 39m

  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
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 24m
    $828–1,142

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

    1. Take the train from Peekskill to 125th Street - Harlemtrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 56m
    $495–940

  9. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Peekskill to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 18m
    $169–625

Peekskill to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration20h 1mAverage Duration
Ticket$127Cheapest Price
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Questions & Answers

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 $120–310 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 Bus Station, and New York Midtown in around 25h 19m.

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