Flights to Chicago with American Airlines from $117*
Popular flights to Chicago
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$
*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.
Testing VGA-2140Ania Liz Prepro
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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)
06/25/25 - 06/29/25
Round trip
I
Economy
from
$237Fare subject to changes
Updated: 14 minutes ago
New York (JFK)to
London (LHR)
04/24/25 - 04/29/25
Round trip
I
Economy
from
$540Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Los Angeles (LAX)
04/30/25 - 05/04/25
Round trip
I
Economy
from
$189Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
London (LHR)
05/07/25 - 05/13/25
Round trip
I
Economy
from
$663Fare subject to changes
Updated: 16 minutes ago
Los Angeles (LAX)to
New York (JFK)
04/30/25 - 05/02/25
Round trip
I
Economy
from
$322Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Miami (MIA)
06/19/25 - 06/22/25
Round trip
I
Economy
from
$374Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Las Vegas (LAS)
06/04/25 - 06/07/25
Round trip
I
Economy
from
$184Fare subject to changes
Updated: 15 minutes ago
Los Angeles (LAX)to
Denver (DEN)
05/27/25 - 05/29/25
Round trip
I
Economy
from
$179Fare subject to changes
Updated: 2 hours ago
Philadelphia (PHL)to
Orlando (MCO)
05/05/25 - 05/07/25
Round trip
I
Economy
from
$208Fare subject to changes
Updated: 29 minutes ago
Dallas (DFW)to
Orlando (MCO)
05/15/25 - 05/19/25
Round trip
I
Economy
from
$331Fare subject to changes
Updated: 53 minutes ago
Dallas (DFW)to
Cancun (CUN)
05/09/25 - 05/12/25
Round trip
I
Economy
from
$356Fare subject to changes
Updated: 46 minutes ago
Miami (MIA)to
Madrid (MAD)
05/07/25 - 05/11/25
Round trip
I
Economy
from
$572Fare subject to changes
Updated: 12 minutes ago
Dallas (DFW)to
Chicago (ORD)
06/06/25 - 06/09/25
Round trip
I
Economy
from
$257Fare subject to changes
Updated: 44 minutes ago
Dallas (DFW)to
Seattle (SEA)
06/17/25 - 06/25/25
Round trip
I
Economy
from
$199Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Miami (MIA)
04/08/25 - 04/10/25
Round trip
I
Economy
from
$335Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Denver (DEN)
05/07/25 - 05/10/25
Round trip
I
Economy
from
$157Fare subject to changes
Updated: 1 hour ago
Philadelphia (PHL)to
Las Vegas (LAS)
04/05/25 - 04/08/25
Round trip
I
Economy
from
$481Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Tokyo (TYO)
05/21/25 - 06/02/25
Round trip
I
Economy
from
$1,128Fare subject to changes
Updated: 2 hours ago
Chicago (ORD)to
Miami (MIA)
06/21/25 - 07/01/25
Round trip
I
Economy
from
$208Fare subject to changes
Updated: 1 hour ago
Philadelphia (PHL)to
Los Angeles (LAX)
04/30/25 - 05/02/25
Round trip
I
Economy
from
$439Fare subject to changes
Updated: 34 minutes ago
DPA to test Miles
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Miles*+taxes and fees
From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 05/28/25 - 06/04/25 | from1 12,000 Miles*+taxes and fees + $12 Updated: 10 hours ago |
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 05/07/25 - 05/12/25 | from1 12,000 Miles*+taxes and fees + $12 Updated: 15 hours ago |
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 07/02/25 - 07/07/25 | from1 14,500 Miles*+taxes and fees + $12 Updated: 19 hours ago |
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 05/06/25 - 05/09/25 | from1 14,500 Miles*+taxes and fees + $12 Updated: 18 hours ago |
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 06/20/25 - 06/22/25 | from1 16,500 Miles*+taxes and fees + $12 Updated: 19 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 07/30/25 - 08/28/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 13 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 07/13/25 - 07/26/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 15 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 07/12/25 - 07/19/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 19 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 07/04/25 - 07/07/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 18 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 09/16/25 - 09/23/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 19 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 04/10/25 - 04/15/25 | from1 15,000 Miles*+taxes and fees + $12 Updated: 13 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 06/06/25 - 06/10/25 | from1 15,500 Miles*+taxes and fees + $12 Updated: 15 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 04/10/25 - 04/17/25 | from1 16,500 Miles*+taxes and fees + $12 Updated: 11 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 06/05/25 - 06/08/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 14 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 06/25/25 - 06/29/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 13 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 09/05/25 - 09/07/25 | from1 12,000 Miles*+taxes and fees + $12 Updated: 9 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 09/18/25 - 09/21/25 | from1 16,500 Miles*+taxes and fees + $12 Updated: 14 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 07/23/25 - 07/28/25 | from1 17,000 Miles*+taxes and fees + $12 Updated: 9 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 06/18/25 - 06/22/25 | from1 18,000 Miles*+taxes and fees + $12 Updated: 18 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 09/23/25 - 09/24/25 | from1 18,000 Miles*+taxes and fees + $12 Updated: 16 hours ago |
DPA to test Miles
DPA test
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| Dallas (DFW) | Chicago (ORD) | Round trip I Economy | 05/07/25 - 05/09/25 | from $147Fare subject to changes Updated: 16 hours ago |
| Phoenix (PHX) | Chicago (ORD) | Round trip I Economy | 05/13/25 - 05/17/25 | from $179Fare subject to changes Updated: 20 hours ago |
| Los Angeles (LAX) | Chicago (ORD) | Round trip I Economy | 05/07/25 - 05/13/25 | from $179Fare subject to changes Updated: 14 hours ago |
| Philadelphia (PHL) | Chicago (ORD) | Round trip I Economy | 06/03/25 - 06/04/25 | from $161Fare subject to changes Updated: 21 hours ago |
| Boston (BOS) | Chicago (ORD) | Round trip I Economy | 04/15/25 - 04/16/25 | from $117Fare subject to changes Updated: 20 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.