American Airlines flights from Chicago

One-way flights from Chicago from $116**

*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.

Round-trip flights to Mexico, Costa Rica and the Caribbean***

Round-trip flights to Mexico, Costa Rica and the Caribbean***
From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)Cancun (CUN)Round trip
I
Economy		10/27/25 - 11/03/25

from

$271Fare subject to changes

Updated: 21 hours ago

Chicago (ORD)Cancun (CUN)Round trip
I
Economy		10/26/25 - 11/02/25

from

$276Fare subject to changes

Updated: 21 hours ago

Chicago (CHI)Cancun (CUN)Round trip
I
Economy		12/05/25 - 12/12/25

from

$309Fare subject to changes

Updated: 22 hours ago

Chicago (CHI)Cancun (CUN)Round trip
I
Economy		12/10/25 - 12/17/25

from

$309Fare subject to changes

Updated: 22 hours ago

Chicago (ORD)Nassau (NAS)Round trip
I
Economy		02/16/26 - 02/22/26

from

$503Fare subject to changes

Updated: 23 hours ago

Chicago (ORD)Nassau (NAS)Round trip
I
Economy		12/16/25 - 12/23/25

from

$505Fare subject to changes

Updated: 22 hours ago

Chicago (ORD)Grand Cayman (GCM)Round trip
I
Economy		01/25/26 - 01/30/26

from

$442Fare subject to changes

Updated: 20 hours ago

Chicago (ORD)Grand Cayman (GCM)Round trip
I
Economy		10/08/25 - 10/15/25

from

$446Fare subject to changes

Updated: 22 hours 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.

Popular flights from Chicago

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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.

Flights from Chicago, IL

American Airlines has flights from Chicago to destinations across the country and around the world. Use flexible search tools to explore our service to major cities like New York, Los Angeles, Dallas-Fort Worth and London. Start planning your next trip with American, according to your schedule, budget or travel style.

Find deals on flights from Chicago

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Chicago (ORD)to

Miami (MIA)
10/22/25 - 10/25/25

Round trip

Economy

from
$157Fare subject to changes
Updated: 17 hours ago

Chicago (ORD)to

Phoenix (PHX)
02/18/26 - 02/25/26

Round trip

Economy

from
$189Fare subject to changes
Updated: 9 hours ago

Chicago (ORD)to

Los Angeles (LAX)
11/05/25 - 11/12/25

Round trip

Economy

from
$197Fare subject to changes
Updated: 13 hours ago

Chicago (ORD)to

Tokyo (TYO)
07/29/26 - 08/06/26

Round trip

Economy

from
$1,551Fare subject to changes
Updated: 10 hours ago

Chicago (ORD)to

Las Vegas (LAS)
01/17/26 - 01/21/26

Round trip

Economy

from
$159Fare subject to changes
Updated: 1 hour ago

Chicago (ORD)to

Dallas (DFW)
11/17/25 - 11/24/25

Round trip

Economy

from
$157Fare subject to changes
Updated: 2 hours 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 from Chicago

Always on the lookout for a good deal on flights from Chicago? By keeping these tips in mind, you can find more affordable options when planning your trip.

  • Book in advance: Booking 1 – 3 months before your departure date can often lead to better deals from Chicago.
  • Travel midweek: Tuesdays and Wednesdays are usually less expensive days to fly since there's less demand.
  • Consider off-peak times: Try flying in late January or early February, when it';s less crowded and prices are more affordable.

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.

Flying from Chicago: what you need to know

How to reach O'Hare International Airport (ORD)

If you're flying out of O'Hare International Airport (ORD) in Chicago, you can get to the airport using public transit, taxis or rideshare apps. Parking options are available for both short-term and long-term stays. Shuttles and private transfers offer added flexibility.

  • CTA Blue Line: The Chicago Transit Authority (CTA) Blue Line rides from downtown Chicago to ORD terminals.
  • Taxis / rideshare: Taxis and rideshare services can take you to designated drop-off zones near the terminal entrances.
  • Hotel shuttles: Many nearby hotels provide shuttle service to the airport. Check in advance for availability.
  • Parking: O'Hare offers several parking garages, including both short-term and long-term parking options. Book in advance to secure your spot.

For more details on parking reservations and other transportation options, be sure to check the official website of O'Hare International Airport.

Airport tips for a smooth flight from Chicago

A little planning goes a long way when it comes to minimizing travel-day stress. Follow these tips and know you're prepared.

  • Arrive early: Plan to arrive at least 2 hours before domestic flights and 3 hours before international trips.
  • Get your boarding pass: Download your boarding pass in the American app or print it before you arrive at the airport.
  • Know your terminal: American typically flies out of Terminal 3. Make sure to check the American app or departure boards at the airport for the correct terminal and gate.
  • Have your ID and travel documents: Travelers need a REAL ID or a valid passport to fly within the U.S. For international travel, a valid passport is required and some international destinations may have additional entry requirements. Check your destination's official website for these requirements.
  • Locate the lounge: Qualified travelers can relax before the runway in the Admirals Club® lounge, with multiple locations throughout Terminal 3. Not a member? Learn more about joining and explore the benefits that come with membership.
  • Find dining options and amenities: ORD offers a variety of restaurants and amenities like a family lounge, mother's rooms and more.

Learn more about how you can manage travel on the go using the American app.

Booking your trip from Chicago on American Airlines

Why wait to start planning your trip from Chicago? American's coast-to-coast flights and international connections are here to support your travel plans, whether you;re heading out for work, fun or a little bit of both. Check out our flexible fares and schedule today.

With an expansive network of destinations, your world is a flight away

To search for a great fare, start by selecting your departure city. Looking to book using miles? Try our miles finder map.

Destinations from Chicago

**Sale to select U.S. destinations from Chicago

  • Limited-time offer. Fares are subject to change.
  • Offer is valid for reservations made in the U.S. for flights originating in the U.S. to select destinations across the U.S.
    • Flights to Nashville (BNA), Albany (ALB), Tulsa (TUL), Palm Springs (PSP), Columbus (CMH), Memphis (MEM), Pittsburgh (PIT), Cincinnati (CVG), Cleveland (CLE) and Kansas City (MCI) from $116 one way.
    • Flights to St. Louis (STL), Omaha (OMA) and Washington, D.C. (WAS) from $119 one way.
    • Flights to Colorado Springs (COS), Rochester (ROC) and Buffalo (BUF) from $126 one way.
    • Flights to Hartford (BDL), Philadelphia (PHL), San Diego (SAN), Austin (AUS), Oklahoma City (OKC), Norfolk (ORF) from $136.
    • Flights to Raleigh (RDU), Charlotte (CLT), Savannah (SAV), Sarasota (SRQ), Providence (PVD), Richmond (RIC), Birmingham (BHM), Charleston (CHS) and Jacksonville (JAX) from $140 one way.
    • Flights to San Antonio (SAT), Tucson (TUS), Albuquerque (ABQ) and El Paso (ELP) from $148 one way.
    • Flights to Los Angeles (LAX), Sacramento (SMF) and Salt Lake City (SLC) from $156 one way.
  • Offer is valid for reservations made from Sept. 15, 2025 to Oct. 12, 2025 at 11:59 p.m. for travel from Jan. 6, 2026 through Feb. 11, 2026.
  • Offer is valid for travel to these destination on Tuesday and Wednesday.
  • This offer cannot be applied retroactively or to existing reservations.
  • Valid only on flights operated by American Airlines and American Eagle.
  • Stopovers are not allowed.
  • Prices include all U.S. government taxes and carrier-imposed fees for travel.
  • Seats and days are limited. Fares may vary by destination, flight and day of week. 
  • Travel may be available for Basic Economy non-refundable fare. Seat assignments made during check-in. May not be eligible for upgrade.  
  • Offer applies only to published, scheduled service. Schedules subject to change.
  • Offer is not combinable with any other offer or promotion.
  • The Terms and Conditions of this promotion, and any element or portion thereof, are subject to change without notice at American Airlines sole discretion.

***Sale to select Mexico, Costa Rica and Caribbean destinations from Chicago

  • Limited-time offer. Fares are subject to change.
  • Offer is valid for reservations made in the U.S. for flights originating in the U.S. to select destinations in Mexico, Costa Rica and the Caribbean.
    • Flights to Cancun (CUN) from $380 round trip.
    • Flights to San Jose, Costa Rica (SJO) from $410 round trip.
    • Flights to Nassau, Bahamas (NAS) from $434 round trip.
    • Flights to Grand Cayman, Cayman Islands (GCM) from $442 round trip.
  • Offer is valid for reservations made from Sept. 15, 2025 to Oct. 12, 2025 at 11:59 p.m. for travel from Jan. 12, 2026 through Feb. 28, 2026.
  • Offer is valid for travel to these destination on Sunday, Monday, Tuesday and Wednesday and from these destinations on Tuesday, Wednesday, Thursday and Friday.
  • This offer cannot be applied retroactively or to existing reservations.
  • Valid only on flights operated by American Airlines and American Eagle.
  • Stopovers are not allowed.
  • Prices include all U.S. government taxes and carrier-imposed fees for travel.
  • Seats and days are limited. Fares may vary by destination, flight and day of week.
  • Travel may be available for Basic Economy non-refundable fare. Seat assignments made during check-in. May not be eligible for upgrade.
  • Offer applies only to published, scheduled service. Schedules subject to change.
  • Offer is not combinable with any other offer or promotion.
  • The Terms and Conditions of this promotion, and any element or portion thereof, are subject to change without notice at American Airlines sole discretion.