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

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

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, subway to Laguardia Airport, fly to Chicago Midway International Airport

    best
    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 20m
    $222–672

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

    cheapest
    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 36m
    $132–492

  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 28m
    $510–870

  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 21m
    $170–260

  5. Drive  819 mi

    1. Drive from Syosset to Chicagocar car 819 mi
    13h 43m
    $145–210

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

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 26m
    $368–878

  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 train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 9m
    $144–704

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

    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 13m
    $133–693

  9. Fly Laguardia Airport to General Mitchell International Airport, train

    1. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 49m
    $187–856

  10. 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 23m
    $185–315

Syosset to Chicago by train

Calendar10Weekly Trains
Duration21h 28mAverage Duration
Ticket$510Cheapest Price
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Comparing Your Travel Options

Map of how to get from Syosset to Chicago.ExpandLaunch map view
  • Distance: 762.4 mi
  • Duration: 5h 20m

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

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 28m. Alternatively, American Airlines and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) every 2 hours.

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