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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 30m
    $215–678

  2. Line 14 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Croton Ave @ S Highland Ave to White Plains Bus Terminal Lane Bbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 1m
    $108–611

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 56m
    $505–809

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 54m
    $146–239

  5. Drive  809.2 mi

    1. Drive from Ossining to Chicagocar car 809.2 mi
    13h 36m
    $148–214

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

    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
    5h 47m
    $145–578

  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 24m
    $337–890

  8. 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 45m
    $158–897

  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 4m
    $200–912

Ossining to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration19h 56mAverage Duration
Ticket$505Cheapest Price
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Comparing Your Travel Options

Map of how to get from Ossining to Chicago.ExpandLaunch map view
  • Distance: 767.3 mi
  • Duration: 5h 30m

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 $500–800 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–230 and the journey takes 20h 25m.

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