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How to get fromNew York to Chicago Loopby plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound, Amtrak)

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There are 10 ways to get from New York to Chicago Loop by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound, Amtrak)

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
    4h 55m
    $208–666

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

    cheapest
    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
    6h 56m
    $124–622

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    19h 32m
    $500–850

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    20h 37m
    $161–235

  5. Drive  789.3 mi

    1. Drive from New York to Chicago Loopcar car 789.3 mi
    13h 10m
    $144–209

  6. 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
    4h 59m
    $134–784

  7. 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 10m
    $138–566

  8. 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 3m
    $326–873

  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
    5h 51m
    $175–975

  10. Bus via Toledo

    1. Take the bus from Port Authority Bus Terminal to Toledo Bus Stopbus bus Greyhound US0420
    2. Take the bus from Toledo to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    21h 32m

New York to Chicago Loop by train (Amtrak)

Calendar10Weekly Trains
Duration19h 32mAverage Duration
Ticket$500Cheapest Price
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Comparing Your Travel Options

Map of how to get from New York to Chicago Loop.ExpandLaunch map view
  • Distance: 747.3 mi
  • Duration: 4h 55m

What companies run services between New York, NY, USA and Chicago Loop, IL, USA?

Southwest Airlines flies from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 2 hours. Alternatively, 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.

Airlines
Train operators
Bus operators

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