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How to get fromWashington Heights to Chicagoby plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, train, or bus (Greyhound)

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There are 10 ways to get from Washington Heights to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, 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 1m
    $218–666

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

    cheapest
    1. Take the train from Fordham to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 42m
    $122–670

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 1m
    $503–853

  4. Bus

    1. Take the bus from New York to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2640 / ...
    21h 20m
    $160–244

  5. Drive  790.6 mi

    1. Drive from Washington Heights to Chicagocar car 790.6 mi
    13h 6m
    $140–202

  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 18m
    $128–486

  7. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 46m
    $140–728

  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 44m
    $369–877

  9. Fly Laguardia Airport to General Mitchell International Airport, train

    1. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 31m
    $183–850

  10. Bus via Baltimore (Greyhound)

    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
    24h 41m
    $173–278

Washington Heights to Chicago by subway and train (Amtrak)

Calendar10Weekly Services
Duration21h 1mAverage Duration
Ticket$503Cheapest Price
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Comparing Your Travel Options

Map of how to get from Washington Heights to Chicago.ExpandLaunch map view
  • Distance: 745 mi
  • Duration: 5h 1m

What companies run services between Washington Heights, New York 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 $500–850 and the journey takes 19h 32m.

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Bus operators

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Need to know: Greyhound

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