Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 ways to get from Harlem 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
    4h 43m
    $90–472

  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
    4h 58m
    $55–262

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 47m
    $123–483

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    22h 25m
    $93–227

  5. Drive 794.1 mi

    1. Drive from Harlem to Chicagocar car 794.1 mi
    13h 10m
    $145–210

  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
    5h 21m
    $75–336

  7. 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 27m
    $818–1,027

  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 49m
    $74–362

  9. 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
    $108–268

Harlem to Chicago by subway and train (Amtrak)

Calendar10Weekly Services
Duration20h 47mAverage Duration
Ticket$123Cheapest Price
See schedules

Questions & Answers

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 $120–480 and the journey takes 19h 32m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers

Where to next?

Trips from Harlem

Trips to Chicago

Popular routes