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

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

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 37m
    $100–512

  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 24m
    $74–307

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 48m
    $293–603

  4. 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 47m
    $158–323

  5. Drive 794.1 mi

    1. Drive from Harlem to Chicagocar car 794.1 mi
    13h 11m
    $145–210

  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
    4h 54m
    $85–352

  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 25m
    $115–366

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

    1. Take the train from 125th Street - Harlem to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 42m
    $89–422

  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 13m
    $138–1,211

  10. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2642 / ...
    24h 24m
    $143–237

Harlem to Chicago by subway and train (Amtrak)

Calendar10Weekly Services
Duration20h 48mAverage Duration
Ticket$293Cheapest Price
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Questions & Answers

Map of how to get from Harlem to Chicago.ExpandLaunch map view
  • Distance: 741.6 mi
  • Duration: 4h 37m

What companies run services between Harlem, 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 $290–600 and the journey takes 19h 32m.

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