American Airlines flights to Chicago from $171*

Popular flights to Chicago on American Airlines

American Airlines offers flights to Chicago (ORD) from cities across the U.S. Nonstop and connecting options are available depending on the route and travel dates, with schedules and fares that vary throughout the year.

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  • New York (LGA)to

    Chicago (ORD)
    07/01/26 - 07/03/26
    from
    $187Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Miami (MIA)to

    Chicago (ORD)
    07/01/26 - 07/08/26
    from
    $201Fare subject to changes
    Updated: 48 minutes ago
    Round trip
    Economy

    Charlotte (CLT)to

    Chicago (ORD)
    06/24/26 - 07/01/26
    from
    $259Fare subject to changes
    Updated: 54 minutes ago
    Round trip
    Economy

    San Francisco (SFO)to

    Chicago (ORD)
    08/04/26 - 08/11/26
    from
    $253Fare subject to changes
    Updated: 44 minutes ago
    Round trip
    Economy

  • New York (NYC)to

    Chicago (ORD)
    06/30/26 - 07/07/26
    from
    $177Fare subject to changes
    Updated: 2 hours ago
    Round trip
    Economy

    Washington, D.C. (DCA)to

    Chicago (ORD)
    07/29/26 - 08/05/26
    from
    $177Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Boston (BOS)to

    Chicago (ORD)
    06/07/26 - 06/09/26
    from
    $192Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Orange County (SNA)to

    Chicago (ORD)
    08/04/26 - 08/11/26
    from
    $289Fare subject to changes
    Updated: 49 minutes ago
    Round trip
    Economy

  • Orlando (MCO)to

    Chicago (ORD)
    07/14/26 - 07/21/26
    from
    $171Fare subject to changes
    Updated: 47 minutes ago
    Round trip
    Economy

    New York/Newark (EWR)to

    Chicago (ORD)
    08/08/26 - 08/15/26
    from
    $177Fare subject to changes
    Updated: 3 hours ago
    Round trip
    Economy

    Tampa (TPA)to

    Chicago (ORD)
    06/23/26 - 06/30/26
    from
    $171Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Las Vegas (LAS)to

    Chicago (ORD)
    06/30/26 - 07/03/26
    from
    $257Fare subject to changes
    Updated: 4 hours ago
    Round trip
    Economy

  • Raleigh (RDU)to

    Chicago (ORD)
    06/23/26 - 06/30/26
    from
    $256Fare subject to changes
    Updated: 58 minutes ago
    Round trip
    Economy

    Denver (DEN)to

    Chicago (ORD)
    07/07/26 - 07/14/26
    from
    $217Fare subject to changes
    Updated: 1 hour ago
    Round trip
    Economy

    Fort Lauderdale (FLL)to

    Chicago (ORD)
    08/12/26 - 08/19/26
    from
    $171Fare subject to changes
    Updated: 55 minutes ago
    Round trip
    Economy

    San Diego (SAN)to

    Chicago (ORD)
    08/19/26 - 08/22/26
    from
    $307Fare subject to changes
    Updated: 17 hours ago
    Round trip
    Economy

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

Visit Chicago, Illinois

Looking for flight deals to Chicago, Illinois? American Airlines offers popular routes to Chicago from many major cities across U.S., including flights from hubs like New York, Los Angeles, Miami, Dallas and Phoenix. Whether you're traveling for business or fun, we make getting to Chicago easy and comfortable. Check out popular flights to Chicago and start planning your visit today.

Find deals on flights to Chicago

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Dallas (DFW)to

Chicago (ORD)
08/11/26 - 08/18/26

Round trip

Economy

from
$280Fare subject to changes
Updated: 41 minutes ago

Los Angeles (LAX)to

Chicago (ORD)
08/04/26 - 08/11/26

Round trip

Economy

from
$201Fare subject to changes
Updated: 56 minutes ago

Phoenix (PHX)to

Chicago (ORD)
07/15/26 - 07/22/26

Round trip

Economy

from
$259Fare subject to changes
Updated: 56 minutes ago

Philadelphia (PHL)to

Chicago (ORD)
07/15/26 - 07/21/26

Round trip

Economy

from
$246Fare subject to changes
Updated: 16 hours ago

Charlotte (CLT)to

Chicago (ORD)
08/04/26 - 08/11/26

Round trip

Economy

from
$259Fare subject to changes
Updated: 54 minutes ago

San Francisco (SFO)to

Chicago (ORD)
07/15/26 - 07/22/26

Round trip

Economy

from
$253Fare subject to changes
Updated: 44 minutes ago

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

Finding cheap flights to Chicago

Looking for lower fares on flights to Chicago? Here are a few ways to save.

  • Book early: Booking 1 to 3 months ahead can help you find lower fares
  • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
  • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

Earn up to $200 back on your next American Airlines flight plus, 40,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

Upgrade your flight with Main Cabin Extra

Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

  • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
  • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
  • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

Discover how Main Cabin Extra can enhance your trip.

American Airlines flights to Chicago

Which airport in Chicago does American Airlines fly to?

Chicago O'Hare International Airport (ORD) is one of the busiest airports in the world and a major hub for American. Located about 17 miles northwest of downtown Chicago, ORD serves as a gateway for both domestic and international travel.

Getting from O'Hare Airport to downtown Chicago

Reaching downtown Chicago from O'Hare International Airport (ORD) is easy and convenient. Whether you're visiting for work or fun, there are plenty of ways to reach your destination. Check out some popular transportation options to discover what works best for your trip.

  • CTA Blue Line 'L' Train: The most affordable choice, operating 24 / 7 and taking about 45 minutes to reach downtown for $5. The station is located in Terminal 2, just a 10 – 15-minute walk from Terminal 3.
  • Taxi / rideshare services: Available from designated areas, costing $35 – $60 and taking around 30 – 40 minutes to reach downtown.

Check out ORD Airport's official website for more details on transportation.

Discover Chicago

Best time to visit Chicago

Chicago offers a vibrant blend of well-known architecture, lakefront beauty and dynamic city energy. From blooming parks in spring to dazzling holiday lights in winter, there's always something to explore throughout the year.

  • Spring (April – June): Enjoy nice weather and plenty of events around the city.
  • Fall (September – October): Experience pleasant temperatures and fewer crowds.

Keep in mind:

  • Summer: Expect larger crowds and higher prices on hotels and events.
  • Winter: Although extremely cold, January and February offer the most affordable flights to Chicago.

Top things to see and do in Chicago

When you fly to Chicago with American Airlines, make sure to explore the city's most iconic landmarks and events. From popular attractions to hidden gems, there are tons of ways to experience the Windy City.

  • Millennium Park: Home to the famous Cloud Gate sculpture, "The Bean".
  • Art Institute of Chicago: A world-class museum and one of the oldest and largest art museums in the United States.
  • Magnificent Mile: A vibrant shopping district with upscale shops, outlets, and trendy restaurants.
  • Field Museum: A must-visit natural history museum, and one of the largest in the world.
  • Shedd Aquarium: This massive aquarium is home to nearly 30,000 animals and is an exciting destination for all ages.

Booking your trip to Chicago with American Airlines

From Millenium Park, deep-dish pizza to buzzing festivals, Chicago has something for every traveler. American Airlines offers the routes and flexibility to help you plan a trip that fits your schedule. Book your flight today and get ready to experience everything the Windy City has to offer.

Chicago routes with American Airlines