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

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There are 8 ways to get from Long Island to Chicago by 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. 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
    3h 11m
    $86–464

  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
    3h 27m
    $52–248

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 56m
    $123–483

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    21h 50m
    $93–233

  5. Drive 794.3 mi

    1. Drive from Brooklyn to Chicagocar car 794.3 mi
    13h 21m
    $145–210

  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
    3h 38m
    $849–996

  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 22m
    $75–336

  8. 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
    23h 42m
    $108–268

Long Island to Chicago by subway, foot, and train (Amtrak)

Calendar10Weekly Services
Duration20h 56mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

What companies run services between Long Island, Suffolk County, 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, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $120–480 and the journey takes 19h 32m.

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