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

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There are 10 ways to get from Islip to Chicago by train, 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 to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Islip to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 27m
    $215–679

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

    cheapest
    1. Take the train from Islip 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 20m
    $126–650

  3. Train

    1. Take the train from Babylon to New York Penn Stationtrain train Babylon Branch / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 26m
    $253–676

  4. Train, bus

    1. Take the train from Amityville to New York Penn Stationtrain train Babylon Branch
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    23h 35m
    $162–253

  5. Drive  835.9 mi

    1. Drive from Islip to Chicagocar car 835.9 mi
    14h 5m
    $153–221

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

    1. Take the train from Islip to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 34m
    $331–885

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

    1. Take the train from Islip to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 44m
    $145–579

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

    1. Take the train from Islip to Jamaicatrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 17m
    $155–910

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

    1. Take the train from Islip to Jamaicatrain 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 1m
    $176–893

  10. Train, bus via Baltimore

    1. Take the train from Babylon 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
    26h 21m
    $178–301

Islip to Chicago by bus and train

Calendar10Weekly Services
Duration22h 26mAverage Duration
Ticket$253Cheapest Price
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Comparing Your Travel Options

Map of how to get from Islip to Chicago.ExpandLaunch map view
  • Distance: 776 mi
  • Duration: 5h 27m

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

You can take a bus from Islip Town Hall to Chicago Union Station via Babylon LIRR, Babylon, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 22h 26m.

Airlines
Train operators
Bus operators

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