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

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

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 Hempstead 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 11m
    $105–507

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

    cheapest
    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 14m
    $71–303

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 27m
    $297–665

  4. Bus via Baltimore

    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 39m
    $163–342

  5. Drive 812.5 mi

    1. Drive from Hempstead to Chicagocar car 812.5 mi
    13h 36m
    $149–215

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

    1. Take the train from Hempstead 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 27m
    $100–277

  7. 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 44m
    $119–337

  8. 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 32m
    $142–1,222

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

    1. Take the train from Hempstead 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 55m
    $102–447

  10. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2642 / ...
    25h 21m
    $143–246

Hempstead to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 27mAverage Duration
Ticket$297Cheapest Price
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Questions & Answers

Map of how to get from Hempstead to Chicago.ExpandLaunch map view
  • Distance: 753.1 mi
  • Duration: 5h 11m

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

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $290–650 and the journey takes 19h 32m. Alternatively, you can take a train from Hempstead to Chicago Bus Station via Jamaica, Sutphin Blvd-Archer Av-JFK Airport, 42 St-Port Authority Bus Terminal, Port Authority Bus Terminal, and Baltimore Downtown Bus Station in around 24h 39m.

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