Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from Hempstead to Chicago by train, subway, plane, train (Amtrak), bus (Flixbus), car, 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. 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
    $210–667

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

    cheapest
    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 59m
    $122–637

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 28m
    $507–865

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    23h 21m
    $144–236

  5. Drive  812.5 mi

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

  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 18m
    $326–873

  7. 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 28m
    $140–567

  8. 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 45m
    $151–898

  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 42m
    $171–993

  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
    $163–262

Hempstead to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 28mAverage Duration
Ticket$507Cheapest Price
See schedules

Comparing Your Travel Options

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 $500–850 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–230 and the journey takes 20h 25m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There