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

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There are 8 ways to get from Chicago to Ossining 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 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 Ossiningtrain
    5h 39m
    $70–278

  2. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak StationtrainLake Shore Limited
    19h 40m
    $116–701

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    23h 58m
    $120–269

  4. Drive 810.2 mi

    1. Drive from Chicago to Ossiningcar810.2 mi
    13h 29m
    $148–214

  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 Ossiningtrain
    5h 22m
    $80–388

  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 Ossiningtrain
    5h 59m
    $776–1,140

  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
    6h 43m
    $112–348

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, line 0014 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)planeORD - HPN
    2. Take the bus from N Broadway @ Main St to Croton Ave @ S Highland Avebus
    7h 21m
    $478–911

Chicago to Ossining by train (Amtrak)

Calendar7Weekly Trains
Duration19h 40mAverage Duration
Ticket$116Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $110–700 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $100–260 and the journey takes 20h 10m.

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