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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 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 Ossiningtrain train
    5h 23m
    $90–458

  2. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    cheapest
    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 Ossiningtrain train
    5h 46m
    $64–278

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    19h 40m
    $167–297

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    23h 57m
    $107–238

  5. Drive 810.2 mi

    1. Drive from Chicago to Ossiningcar car 810.2 mi
    13h 38m
    $148–214

  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)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Ossiningtrain train
    6h
    $826–1,040

  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 42m
    $96–383

  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)plane plane ORD - HPN
    2. Take the bus from Martine Ave @ Court St to Croton Ave @ S Highland Avebus bus
    7h 15m
    $84–451

Chicago to Ossining by train (Amtrak)

Calendar7Weekly Trains
Duration19h 40mAverage Duration
Ticket$167Cheapest 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 $160–290 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $95–230 and the journey takes 20h 10m.

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