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How to get fromSyosset to Chicagoby plane, train (Amtrak), train, bus, car or subway

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There are 10 ways to get from Syosset to Chicago by plane, train (Amtrak), train, bus, car, or subway

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 John F. Kennedy International Airport to Chicago O'Hare International Airport

    best
    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    5h 21m
    $768–1,128

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

    cheapest
    1. Take the train from Syosset to Jamaicatrain
    2. Take the subway from Sutphin Blvd-Archer Av-JFK Airport to Jackson Hts-Roosevelt Avsubway
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 31m
    $67–272

  3. Train

    1. Take the train from Syosset to New York Penn StationtrainPort Jefferson Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union StationtrainLake Shore Limited / ...
    21h 29m
    $139–570

  4. Train, bus

    1. Take the train from Syosset to New York Penn StationtrainPort Jefferson Branch
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    22h 22m
    $104–230

  5. Drive 819 mi

    1. Drive from Syosset to Chicagocar819 mi
    13h 34m
    $150–216

  6. Train, subway to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Syosset to Jamaicatrain
    2. Take the subway from Sutphin Blvd-Archer Av-JFK Airport to Jackson Hts-Roosevelt Avsubway
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 20m
    $87–422

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

    1. Take the train from Syosset to New York Penn Stationtrain
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    6h 1m
    $91–313

  8. Train to Newark Liberty International Airport, fly to Chicago Midway International Airport

    1. Take the train from Syosset to New York Penn Stationtrain
    2. Fly from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)planeEWR - MDW
    5h 51m
    $96–413

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

    1. Take the train from Syosset to Jamaicatrain
    2. Take the train from Jamaica to Grand Central Terminaltrain
    3. Take the train from Grand Central Terminal to White Plainstrain
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    8h 13m
    $93–423

  10. Train, bus via Baltimore

    1. Take the train from Syosset to New York Penn Stationtrain
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    24h 38m
    $119–345

Syosset to Chicago by train

Calendar10Weekly Trains
Duration21h 29mAverage Duration
Ticket$139Cheapest Price
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Questions & Answers

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

American Airlines, JetBlue Airways, and two other airlines fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) every 2 hours. Alternatively, you can take a train from Syosset to Chicago Union Station via Penn Station and Ny Moynihan Train Hall At Penn Station in around 21h 29m.

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