Flights to Chicago with American Airlines from USD387*
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1 Adult, Economy class
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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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Please use the search function at the top of the page to find our best flight deals
Please use the search function at the top of the page to find our best flight deals*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
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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USD
Dallas (DFW)to
New York (LGA)
08/04/25 - 08/07/25
Round trip
Economy
from
USD179Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
London (LHR)
08/12/25 - 08/26/25
Round trip
Economy
from
USD618Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Los Angeles (LAX)
08/01/25 - 08/08/25
Round trip
Economy
from
USD195Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Miami (MIA)
08/19/25 - 08/26/25
Round trip
Economy
from
USD131Fare subject to changes
Updated: 2 hours ago
Los Angeles (LAX)to
New York (JFK)
09/13/25 - 09/17/25
Round trip
Economy
from
USD199Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Melbourne (MEL)
08/19/25 - 08/26/25
Round trip
Economy
from
USD1,076Fare subject to changes
Updated: 2 minutes ago
Phoenix (PHX)to
Flagstaff (FLG)
08/05/25 - 08/12/25
Round trip
Economy
from
USD267Fare subject to changes
Updated: 3 hours ago
New York (JFK)to
London (LHR)
10/01/25 - 10/06/25
Round trip
Economy
from
USD488Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Denver (DEN)
07/13/25 - 07/18/25
Round trip
Economy
from
USD347Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Las Vegas (LAS)
08/24/25 - 08/29/25
Round trip
Economy
from
USD159Fare subject to changes
Updated: 2 hours ago
Philadelphia (PHL)to
Orlando (MCO)
09/24/25 - 09/28/25
Round trip
Economy
from
USD224Fare subject to changes
Updated: 2 hours ago
Phoenix (PHX)to
Miami (MIA)
08/28/25 - 09/02/25
Round trip
Economy
from
USD303Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Orlando (MCO)
09/22/25 - 09/26/25
Round trip
Economy
from
USD159Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Boston (BOS)
08/09/25 - 08/16/25
Round trip
Economy
from
USD157Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Cancun (CUN)
09/26/25 - 10/01/25
Round trip
Economy
from
USD305Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Chicago (ORD)
07/20/25 - 07/27/25
Round trip
Economy
from
USD268Fare subject to changes
Updated: 32 minutes ago
Dallas (DFW)to
Denver (DEN)
09/30/25 - 10/07/25
Round trip
Economy
from
USD137Fare subject to changes
Updated: 2 hours ago
Philadelphia (PHL)to
Los Angeles (LAX)
09/06/25 - 09/10/25
Round trip
Economy
from
USD199Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
San Francisco (SFO)
07/23/25 - 08/01/25
Round trip
Economy
from
USD275Fare subject to changes
Updated: 2 hours ago
Miami (MIA)to
Madrid (MAD)
09/24/25 - 10/01/25
Round trip
Economy
from
USD358Fare subject to changes
Updated: 1 hour ago
DPA test
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From | To | Fare type | Travel dates | Price |
|---|---|---|---|---|
| San Juan (SJU) | Chicago (ORD) | Round trip I Economy | 09/29/25 - 10/06/25 | from USD387Fare subject to changes Updated: 6 hours ago |
| San Juan (SJU) | Chicago (CHI) | Round trip I Economy | 08/16/25 - 08/23/25 | from USD387Fare subject to changes Updated: 4 hours ago |
Title Chicago -  - the United States - American Airlines - test
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.
QA FE Testing VGA-2495 Prepro
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USD
Dallas (DFW)to
New York (LGA)09/06/25 - 09/18/25fromUSD179Fare subject to changesUpdated: 10 minutes agoRound tripEconomy
Dallas (DFW)to
London (LHR)08/12/25 - 08/26/25fromUSD618Fare subject to changesUpdated: 1 hour agoRound tripEconomy
Dallas (DFW)to
Los Angeles (LAX)07/29/25 - 08/05/25fromUSD195Fare subject to changesUpdated: 2 hours agoRound tripEconomy
Dallas (DFW)to
Miami (MIA)08/19/25 - 08/26/25fromUSD131Fare subject to changesUpdated: 2 hours agoRound tripEconomy
QA FE Asset in CP VGA-2437
QA FE VGA-2494
Dallas (DFW)to
New York (LGA)
08/04/25 - 08/07/25
Round trip
Economy
from
USD179Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
London (LHR)
08/12/25 - 08/26/25
Round trip
Economy
from
USD618Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Los Angeles (LAX)
08/01/25 - 08/08/25
Round trip
Economy
from
USD195Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Miami (MIA)
08/19/25 - 08/26/25
Round trip
Economy
from
USD131Fare subject to changes
Updated: 2 hours ago
Los Angeles (LAX)to
New York (JFK)
09/13/25 - 09/17/25
Round trip
Economy
from
USD199Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Melbourne (MEL)
08/19/25 - 08/26/25
Round trip
Economy
from
USD1,076Fare subject to changes
Updated: 2 minutes ago
Phoenix (PHX)to
Flagstaff (FLG)
08/05/25 - 08/12/25
Round trip
Economy
from
USD267Fare subject to changes
Updated: 3 hours ago
New York (JFK)to
London (LHR)
10/01/25 - 10/06/25
Round trip
Economy
from
USD488Fare subject to changes
Updated: 1 hour ago
Los Angeles (LAX)to
Denver (DEN)
07/13/25 - 07/18/25
Round trip
Economy
from
USD347Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Las Vegas (LAS)
08/24/25 - 08/29/25
Round trip
Economy
from
USD159Fare subject to changes
Updated: 2 hours ago
Philadelphia (PHL)to
Orlando (MCO)
09/24/25 - 09/28/25
Round trip
Economy
from
USD224Fare subject to changes
Updated: 2 hours ago
Phoenix (PHX)to
Miami (MIA)
08/28/25 - 09/02/25
Round trip
Economy
from
USD303Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Orlando (MCO)
09/22/25 - 09/26/25
Round trip
Economy
from
USD159Fare subject to changes
Updated: 1 hour ago
Dallas (DFW)to
Boston (BOS)
08/09/25 - 08/16/25
Round trip
Economy
from
USD157Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Cancun (CUN)
09/26/25 - 10/01/25
Round trip
Economy
from
USD305Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
Chicago (ORD)
07/20/25 - 07/27/25
Round trip
Economy
from
USD268Fare subject to changes
Updated: 32 minutes ago
Dallas (DFW)to
Denver (DEN)
09/30/25 - 10/07/25
Round trip
Economy
from
USD137Fare subject to changes
Updated: 2 hours ago
Philadelphia (PHL)to
Los Angeles (LAX)
09/06/25 - 09/10/25
Round trip
Economy
from
USD199Fare subject to changes
Updated: 2 hours ago
Dallas (DFW)to
San Francisco (SFO)
07/23/25 - 08/01/25
Round trip
Economy
from
USD275Fare subject to changes
Updated: 2 hours ago
Miami (MIA)to
Madrid (MAD)
09/24/25 - 10/01/25
Round trip
Economy
from
USD358Fare subject to changes
Updated: 1 hour ago