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

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There are 9 ways to get from Ossining 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 Ossining to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 45m
    $99–488

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

    cheapest
    1. Take the train from Ossining to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 1m
    $64–278

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 56m
    $71–370

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    24h 57m
    $103–236

  5. Drive 809.2 mi

    1. Drive from Ossining to Chicagocar car 809.2 mi
    13h 35m
    $148–214

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

    1. Take the train from Ossining 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 47m

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

    1. Take the train from Ossining 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 28m
    $826–1,039

  8. Line 0019 bus, train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Croton Ave @ S Highland Ave to Bedford Rd @ Wheeler Avebus bus
    2. Take the train from Pleasantville to White Plainstrain train
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 5m
    $75–363

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

    1. Take the train from Ossining to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 17m
    $226–693

Ossining to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration19h 56mAverage Duration
Ticket$71Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $65–360 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $90–220 and the journey takes 20h 25m.

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