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How to get fromMassapequa to Chicagoby train, plane, bus, train (Amtrak), or car

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There are 10 ways to get from Massapequa to Chicago by train, plane, bus, train (Amtrak), or car

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 Massapequa to Woodsidetrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4h 59m
    $213–624

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

    cheapest
    1. Take the train from Massapequa to Grand Central Terminaltrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 56m
    $123–592

  3. Train, bus

    1. Take the train from Massapequa to New York Penn Stationtrain train Babylon Branch
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    18h 45m
    $129–229

  4. Train

    1. Take the train from Massapequa to New York Penn Stationtrain train Babylon Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 22m
    $289–669

  5. Drive 817.7 mi

    1. Drive from Massapequa to Chicagocar car 817.7 mi
    13h 54m
    $150–216

  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 15m
    $328–877

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

    1. Take the train from Massapequa to Woodsidetrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 19m
    $143–574

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

    1. Take the train from Massapequa to New York Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 54m
    $152–902

  9. Train, train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Massapequa to New York Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 46m
    $174–997

  10. Train, bus via Baltimore

    1. Take the train from Massapequa to New York Penn Stationtrain train
    2. Take the bus from New York to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 17m
    $154–349

Massapequa to Chicago by train and bus

Calendar15Weekly Services
Duration18h 45mAverage Duration
Ticket$129Cheapest Price
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Questions & Answers

Map of how to get from Massapequa to Chicago.ExpandLaunch map view
  • Distance: 762.6 mi
  • Duration: 4h 59m

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

You can take a train from Massapequa to Chicago Union Station via Penn Station and Ny Moynihan Train Hall At Penn Station in around 21h 22m. Alternatively, American Airlines, JetBlue Airways, and Delta fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) hourly.

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