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How to get fromJamaica to Chicagoby plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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There are 10 ways to get from Jamaica to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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
    4h 43m
    $321–864

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

    cheapest
    1. Take the train from Jamaica to Grand Central Terminaltrain train
    2. Take the train from Grand Central Terminal to White Plainstrain train
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 29m
    $129–632

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 52m
    $505–859

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    21h 45m
    $155–249

  5. Drive  799.2 mi

    1. Drive from Jamaica to Chicagocar car 799.2 mi
    13h 29m
    $146–211

  6. Fly Laguardia Airport to Chicago Midway International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h
    $208–666

  7. Fly Laguardia Airport to Chicago O'Hare International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 22m
    $138–566

  8. Fly Newark Liberty International Airport to Chicago O'Hare International Airport

    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 33m
    $139–793

  9. Train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain train
    2. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 22m
    $179–988

  10. Bus via Baltimore (Greyhound)

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    24h 54m
    $173–268

Jamaica to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration20h 52mAverage Duration
Ticket$505Cheapest Price
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Comparing Your Travel Options

Map of how to get from Jamaica to Chicago.ExpandLaunch map view
  • Distance: 761 mi
  • Duration: 4h 43m

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

American Airlines and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $500–850 and the journey takes 19h 32m.

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Train operators
Bus operators

Want to know more about travelling around United States

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