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

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There are 10 ways to get from Lower Manhattan 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 6m
    $97–515

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

    cheapest
    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 27m
    $54–267

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 50m
    $273–603

  4. Bus (Flixbus)

    1. Take the bus from New York City Chinatown to Chicago Bus Stationbus bus FlixBus N2640
    21h 10m
    $130–230

  5. Drive 788.2 mi

    1. Drive from Lower Manhattan to Chicagocar car 788.2 mi
    13h 9m
    $144–208

  6. Fly Laguardia Airport to Chicago O'Hare International Airport

    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 23m
    $57–295

  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 19m
    $75–306

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

    1. Take the train from Grand Central Terminal to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 18m
    $457–626

  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 33m
    $115–1,161

  10. 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 45m
    $178–373

Lower Manhattan to Chicago by subway, foot, and train (Amtrak)

Calendar10Weekly Services
Duration20h 50mAverage Duration
Ticket$273Cheapest Price
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Questions & Answers

What companies run services between Lower Manhattan, 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 $270–600 and the journey takes 19h 32m.

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