American Airlines flights to Chicago from $91*

Popular flights to Chicago on American Airlines

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*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)
08/16/25 - 08/23/25

Round trip

Economy

from
$157Fare subject to changes
Updated: 32 minutes ago

Los Angeles (LAX)to

Chicago (ORD)
09/02/25 - 09/09/25

Round trip

Economy

from
$197Fare subject to changes
Updated: 20 minutes ago

Phoenix (PHX)to

Chicago (ORD)
08/23/25 - 08/30/25

Round trip

Economy

from
$189Fare subject to changes
Updated: 15 minutes ago

Philadelphia (PHL)to

Chicago (ORD)
10/07/25 - 10/14/25

Round trip

Economy

from
$151Fare subject to changes
Updated: 14 minutes ago

New York (LGA)to

Chicago (ORD)
09/03/25 - 09/10/25

Round trip

Economy

from
$142Fare subject to changes
Updated: 13 hours ago

Miami (MIA)to

Chicago (ORD)
09/16/25 - 09/23/25

Round trip

Economy

from
$137Fare subject to changes
Updated: 17 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.

Tips for finding cheap flights to Chicago

Planning a trip to Chicago? American Airlines offers great prices and plenty of options, whether you're booking early or flying last minute.

  • Book early: Secure great prices by booking your flights at least 1 – 3 months in advance.
  • Be flexible with dates: Midweek flights, especially on Tuesdays and Wednesdays, often offer cheaper fares.
  • Travel off-peak: Consider flying during less-busy months, such as January and February, for more affordable flights to Chicago, Illinois.

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 from **Flights.FromLowestPrice***

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.

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