Flights to Chicago with American Airlines from $97*
Popular flights to Chicago
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*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. Additional bag and optional fees for products and services may apply.
Find deals on flights to Chicago
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 17/10/2025 - 23/10/2025 | from $397Fare subject to changes Updated: 14 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 08/10/2025 - 12/10/2025 | from $427Fare subject to changes Updated: 15 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 14/11/2025 - 18/11/2025 | from $333Fare subject to changes Updated: 11 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 07/10/2025 - 10/10/2025 | from $375Fare subject to changes Updated: 14 hours ago |
| Charlotte (CLT) | Chicago (ORD) | Round trip I Economy | 16/10/2025 - 18/10/2025 | from $353Fare subject to changes Updated: 15 hours ago |
| Miami (MIA) | Chicago (ORD) | Round trip I Economy | 15/11/2025 - 19/11/2025 | from $333Fare subject to changes Updated: 16 hours ago |
| Boston (BOS) | Chicago (ORD) | Round trip I Economy | 22/10/2025 - 27/10/2025 | from $117Fare subject to changes Updated: 15 hours ago |
| Fort Myers (RSW) | Chicago (ORD) | Round trip I Economy | 30/01/2026 - 02/02/2026 | from $357Fare subject to changes Updated: 14 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.
Chicago routes with American Airlines
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Fly to Chicago with American Airlines
Arriving in Chicago
Chicago is one of the United States’ premiere destinations. Book your flights to Chicago and get ready to wander through its innovative parks, diverse museums, plethora of stores and boutiques, and fantastic restaurants. Visit American Airlines.com to find flight deals to Chicago.
First Time in Chicago
No trip to Chicago is complete without a visit to Millennium Park. A mix of cutting-edge art and landscape design, the park provides the backdrop for hundreds of live performances, tours, and family fun all year long. Within the park, the Lurie Garden encompasses five acres of gorgeous greenery and is a focal point of the city.
Your Chicago
Travelers young and old will love the Peggy Notebaert Nature Museum. A recreated prairie, rooftop gardens, and the Judy Istock Butterfly Haven make this one of the most interactive and unique museums in the world. Reserve your tickets to Chicago and immerse yourself in this city of traditional delights and modern amenities.
Making the Most of Your Chicago Holiday
Chicago has four distinct seasons each year. To avoid excessive crowds, visitors may want to travel to Chicago during the winter. Temperatures can be very cold and snowy, but attractions will be more accessible, and cheap hotels in Chicago much easier to find.
Testing CMS-2860 Ania Liz (Two Column-Prepro)
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Dallas (DFW)to
New York (LGA)
10/05/2025 - 17/05/2025
Round trip
I
Economy
from
$197Fare subject to changes
Updated: 1 hour ago
New York (JFK)to
London (LHR)
05/05/2025 - 10/06/2025
Round trip
I
Economy
from
$567Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
London (LHR)
08/06/2025 - 08/07/2025
Round trip
I
Economy
from
$784Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Los Angeles (LAX)
24/06/2025 - 01/07/2025
Round trip
I
Economy
from
MXN3,576Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Miami (MIA)
24/06/2025 - 01/07/2025
Round trip
I
Economy
from
$219Fare subject to changes
Updated: 7 minutes ago
Los Angeles (LAX)to
New York (JFK)
06/05/2025 - 07/05/2025
Round trip
I
Economy
from
$257Fare subject to changes
Updated: 29 minutes ago
Los Angeles (LAX)to
Denver (DEN)
22/05/2025 - 26/05/2025
Round trip
I
Economy
from
$321Fare subject to changes
Updated: 1 hour ago
Philadelphia (PHL)to
Orlando (MCO)
25/04/2025 - 27/04/2025
Round trip
I
Economy
from
$277Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Las Vegas (LAS)
28/05/2025 - 31/05/2025
Round trip
I
Economy
from
$159Fare subject to changes
Updated: 1 hour ago
Phoenix (PHX)to
Miami (MIA)
26/04/2025 - 28/04/2025
Round trip
I
Economy
from
$297Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Melbourne (MEL)
07/05/2025 - 26/05/2025
Round trip
I
Economy
from
$1,394Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Orlando (MCO)
19/06/2025 - 24/06/2025
Round trip
I
Economy
from
$257Fare subject to changes
Updated: 1 hour ago
Miami (MIA)to
Madrid (MAD)
01/05/2025 - 05/05/2025
Round trip
I
Economy
from
$584Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Cancun (CUN)
26/04/2025 - 30/04/2025
Round trip
I
Economy
from
$436Fare subject to changes
Updated: 2 hours ago
Los Angeles (LAX)to
London (LHR)
10/05/2025 - 19/05/2025
Round trip
I
Economy
from
$591Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Boston (BOS)
21/05/2025 - 28/05/2025
Round trip
I
Economy
from
$242Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Chicago (ORD)
07/06/2025 - 09/06/2025
Round trip
I
Economy
from
$237Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Seattle (SEA)
24/04/2025 - 26/04/2025
Round trip
I
Economy
from
$258Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Tokyo (TYO)
12/05/2025 - 28/05/2025
Round trip
I
Economy
from
$914Fare subject to changes
Updated: 1 hour ago
Philadelphia (PHL)to
Las Vegas (LAS)
29/05/2025 - 31/05/2025
Round trip
I
Economy
from
$349Fare subject to changes
Updated: 1 hour ago
DPA test
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 29/04/2025 - 06/05/2025 | from $147Fare subject to changes Updated: 13 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 10/05/2025 - 17/05/2025 | from $179Fare subject to changes Updated: 5 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 10/05/2025 - 17/05/2025 | from $179Fare subject to changes Updated: 13 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 02/07/2025 - 05/07/2025 | from $169Fare subject to changes Updated: 8 hours ago |
| New York (LGA) | Chicago (ORD) | Round trip I Economy | 27/05/2025 - 03/06/2025 | from $157Fare subject to changes Updated: 5 hours ago |
AAV Vacation Packages with promo code: HOLIDAY2024
*Offer: $150
*Minimum spend: $5,000
*Minimum stay: 4 nights
*Booking dates: 11/16/2024 through 11/30/2024
*Travel dates: 11/18/2024 through 9/30/2025
*Blackout dates: 11/28/2024, 12/25/2024, 12/31/2024, 1/1/2025, 4/20/2025, 5/26/2025, 7/4/2025, 9/1/2025
To receive the offer, purchase a vacation package from 11/16/2024 through 11/30/2024. The package must include round-trip flights. The offer is valid for new reservations made during the promotional booking period. All travel must start after 11/18/2024 and finish by 9/30/2025 for promotion to apply. Multiple hotel stays are valid for promo as long as the total nights booked are greater than the minimum stay requirements.
The promotion code cannot be honored retroactively or applied to existing reservations. The promotion code is only valid for reservations booked online at aavacations.com or by calling 1-800-321-2121. Only one promotion code may be entered per booking. Rates, travel dates and advance reservation requirements vary per room. Rates may vary depending on travel dates. Blackout dates and other significant restrictions may apply. Vacation packages include government-imposed hotel taxes; some hotels may impose other fees at checkout in addition to the taxes and fees included in this offer. Offer is not valid for group travel, is not combinable, and may be withdrawn or modified at any time. When booking air and hotel together, the hotel stay must match the itinerary dates of the air booked or must have a minimum of 4 nights hotel. The hotel in the package must be located in the passenger's vacation destination.