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How to get fromWesthampton Beach to Chicagoby train, plane, bus (Flixbus), train (Amtrak), car, car ferry, or bus (Greyhound)

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There are 9 ways to get from Westhampton Beach to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, car ferry, 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 to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Speonk to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 22m
    $267–752

  2. Drive  865.5 mi

    cheapest
    1. Drive from Westhampton Beach to Chicagocar car 865.5 mi
    14h 41m
    $158–229

  3. Bus

    1. Take the bus from Westhampton to 3 Av & 39 Stbus bus Westhampton
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 24m
    $179–315

  4. Train

    1. Take the train from Westhampton to New York Penn Stationtrain train Montauk Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 40m
    $297–678

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

    1. Take the train from Speonk to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 35m
    $197–652

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

    1. Take the train from Speonk to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 30m
    $383–958

  7. Drive, car ferry to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Drive from Westhampton Beach to Port Jeffersoncar car
    2. Take the carferry from Port Jefferson to Bridgeportcarferry car ferry
    3. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 59m
    $204–649

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

    1. Take the train from Speonk to Jamaicatrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 12m
    $178–673

  9. Bus via Baltimore

    1. Take the bus from Westhampton to 3 Av & 42 Stbus bus
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    29h 32m
    $189–380

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar68Weekly Planes
Duration2h 41mAverage Duration
Ticket$93Cheapest Price
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Questions & Answers

Map of how to get from Westhampton Beach to Chicago.ExpandLaunch map view
  • Distance: 807.9 mi
  • Duration: 6h 22m

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

You can take a vehicle from Westhampton Beach to Chicago Bus Station via Westhampton, 3 Av & 39 St, E 34 St/3 Av, W 34 St/7 Av, and New York Midtown in around 20h 24m. Alternatively, you can take a vehicle from Westhampton Beach to Chicago Union Station via Westhampton, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 22h 40m.

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