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

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There are 9 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)plane plane JFK - ORD
    5h 16m
    $328–878

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

    cheapest
    1. Take the train from Syosset to Jamaicatrain train
    2. Take the train from Jamaica to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to White Plainstrain train
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 5m
    $118–593

  3. Train

    1. Take the train from Syosset to New York Penn Stationtrain train Port Jefferson Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 29m
    $240–570

  4. Train, bus

    1. Take the train from Syosset to New York Penn Stationtrain train Port Jefferson Branch
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    22h 22m
    $150–250

  5. Drive  819 mi

    1. Drive from Syosset to Chicagocar car 819 mi
    13h 43m
    $150–216

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

    1. Take the train from Syosset to Jamaicatrain train
    2. Take the subway from Sutphin Blvd-Archer Av-JFK Airport to Jackson Hts-Roosevelt Avsubway subway
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 25m
    $142–572

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

    1. Take the train from Syosset to Jamaicatrain train
    2. Take the subway from Sutphin Blvd-Archer Av-JFK Airport to Jackson Hts-Roosevelt Avsubway subway
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 16m
    $212–672

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

    1. Take the train from Syosset to New York Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 2m
    $153–903

  9. Train, bus via Baltimore

    1. Take the train from Syosset to New York Penn Stationtrain train
    2. Take the bus from New York to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 24m
    $165–295

Syosset to Chicago by train

Calendar10Weekly Trains
Duration21h 29mAverage Duration
Ticket$240Cheapest Price
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Comparing Your Travel Options

Map of how to get from Syosset to Chicago.ExpandLaunch map view
  • Distance: 780.8 mi
  • Duration: 5h 16m

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

American Airlines, JetBlue Airways, and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) hourly. 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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