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

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

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 16m
    $220–667

  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 32m
    $130–487

  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
    $507–865

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    23h 21m
    $154–246

  5. Drive  812.5 mi

    1. Drive from Hempstead to Chicagocar car 812.5 mi
    13h 36m
    $144–208

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

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 22m
    $366–873

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

    1. Take the train from Mineola to New York Penn Stationtrain train
    2. Take the train from New York Penn Station to Newark Airport Railroad Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 52m
    $141–698

  8. 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
    8h 5m
    $132–687

  9. Fly Laguardia Airport to General Mitchell International Airport, train

    1. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 45m
    $185–851

  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
    25h 30m
    $178–287

Hempstead to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 27mAverage Duration
Ticket$507Cheapest Price
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Comparing Your Travel Options

Map of how to get from Hempstead to Chicago.ExpandLaunch map view
  • Distance: 753.1 mi
  • Duration: 5h 16m

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 2 hours. 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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