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How to get fromChicago to Jamaicaby plane, bus (Flixbus), train (Amtrak), car, train, or bus (Greyhound)

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There are 11 ways to get from Chicago to Jamaica by plane, bus (Flixbus), train (Amtrak), 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 Chicago Midway International Airport to Laguardia Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    4h 17m
    $206–658

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to Jamaicatrain train
    7h 8m
    $104–482

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    17h 28m
    $129–208

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    20h 35m
    $265–578

  5. Drive 799.4 mi

    1. Drive from Chicago to Jamaicacar car 799.4 mi
    13h 32m
    $146–211

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

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    4h 18m
    $322–864

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    4h 40m
    $136–558

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Airport Railroad Station to New York Penn Stationtrain train
    3. Take the train from New York Penn Station to Jamaicatrain train
    5h 8m
    $148–893

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

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Laguardia Airport (LGA)plane plane MKE - LGA
    5h 58m
    $178–867

  10. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    6h 12m
    $170–988

  11. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0164
    2. Take the bus from Baltimore to New Yorkbus bus Ppb 8724 / ...
    22h 58m
    $160–312

Chicago to Jamaica by bus and train (Flixbus)

Calendar16Weekly Services
Duration17h 28mAverage Duration
Ticket$129Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Jamaica.ExpandLaunch map view
  • Distance: 742.6 mi
  • Duration: 4h 17m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) every 4 hours. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $120–200 and the journey takes 17h 5m.

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