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

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There are 10 ways to get from Hempstead to Chicago 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 Laguardia Airport to Chicago Midway International Airport

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4h 49m
    $141–569

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

    cheapest
    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 4m
    $96–489

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    19h 51m
    $133–226

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 38m
    $320–667

  5. Drive 812.5 mi

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

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

    1. Take the train from Hempstead to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 45m
    $406–873

  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
    $129–697

  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 31m
    $172–1,022

  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
    $102–457

  10. 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
    25h 16m
    $161–336

Hempstead to Chicago by bus and foot (Flixbus)

Calendar7Weekly Services
Duration19h 51mAverage Duration
Ticket$133Cheapest Price
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Questions & Answers

Map of how to get from Hempstead to Chicago.ExpandLaunch map view
  • Distance: 752.9 mi
  • Duration: 4h 49m

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

Southwest Airlines and Delta fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $130–220 and the journey takes 16h 55m.

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