CHI

Find cheap American Airlines flights to Chicago from $88

1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap American Airlines Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from American Airlines to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip American Airlines flight deals to Chicago

Sat, Jul 11 - Tue, Jul 14
American Airlines Logo
1:50 pm - 3:46 pm
JFK
-
ORD
2h 56mnonstop
American Airlines Logo
4:26 pm - 8:00 pm
ORD
-
JFK
2h 34mnonstop
$177American Airlines
Thu, Jun 25 - Sun, Jun 28
American Airlines Logo
5:30 am - 7:15 am
EWR
-
ORD
2h 45mnonstop
American Airlines Logo
6:47 am - 10:02 am
ORD
-
EWR
2h 15mnonstop
$177American Airlines
Wed, Jul 22 - Fri, Jul 24
American Airlines Logo
7:23 am - 9:10 am
LGA
-
ORD
2h 47mnonstop
American Airlines Logo
6:00 am - 9:13 am
ORD
-
LGA
2h 13mnonstop
$177American Airlines
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
5:30 am - 7:17 am
EWR
-
ORD
2h 47mnonstop
American Airlines Logo
6:50 am - 10:02 am
ORD
-
EWR
2h 12mnonstop
$178American Airlines
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
6:29 am - 8:20 am
LGA
-
ORD
2h 51mnonstop
American Airlines Logo
8:23 pm - 11:40 pm
ORD
-
LGA
2h 17mnonstop
$178American Airlines
Sat, Jun 6 - Sat, Jun 13
American Airlines Logo
9:59 am - 11:47 am
JFK
-
ORD
2h 48mnonstop
American Airlines Logo
4:44 pm - 8:15 pm
ORD
-
JFK
2h 31mnonstop
$182American Airlines
Wed, Jun 10 - Thu, Jun 18
American Airlines Logo
6:59 am - 8:46 am
EWR
-
ORD
2h 47mnonstop
American Airlines Logo
8:15 pm - 11:30 pm
ORD
-
EWR
2h 15mnonstop
$182American Airlines
Tue, May 5 - Tue, May 5
American Airlines Logo
12:00 pm - 1:49 pm
LGA
-
ORD
2h 49mnonstop
American Airlines Logo
5:38 pm - 8:59 pm
ORD
-
LGA
2h 21mnonstop
$182American Airlines
Sat, Jun 27 - Mon, Jun 29
American Airlines Logo
5:30 am - 7:15 am
EWR
-
ORD
2h 45mnonstop
American Airlines Logo
8:15 pm - 11:30 pm
ORD
-
EWR
2h 15mnonstop
$183American Airlines
Tue, May 5 - Tue, May 5
American Airlines Logo
12:00 pm - 1:49 pm
LGA
-
ORD
2h 49mnonstop
American Airlines Logo
5:38 pm - 8:59 pm
ORD
-
LGA
2h 21mnonstop
$183American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$89
Average price round-trip$290
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport
(price for this month)

When to book flights with American Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with American Airlines

  • Which other airlines fly to Chicago?

    Along with American Airlines, you can also fly to Chicago with United Airlines, Southwest, Allegiant Air, Contour, United Airlines, Frontier, Frontier, Delta, Alaska Airlines, Avelo Airlines, Denver Air Connection, Contour and Allegiant Air.

  • How much is a flight to Chicago with American Airlines?

    On average, American Airlines flights to Chicago cost $354 one-way.

  • Which airport do American Airlines flights to Chicago fly into?

    American Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in oneworld that fly to Chicago?

    The only other oneworld airline flying to Chicago is Alaska Airlines.

Top tips for your flights to Chicago with American Airlines

  • The cheapest flight to Chicago with American Airlines found on KAYAK in the last 2 weeks departed from Manchester and cost $153.
  • If you’re intending to fly with American Airlines, book your flight to Chicago at least 2 weeks before departure to ensure a below-average price.
  • High season for flights to Chicago with American Airlines is July and prices are highest at this time. The cheapest month to fly is January.

American Airlines customer reviews

7.1
Good10,000 verified ratings
7.2Comfort
6.9Entertainment
7.5Boarding
6.4Food
7.9Crew
Traveler rating:
Sort by:
L
2.0 Poor
Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —
L
2.0 Poor
Internet not working. Flight delayed
A
10.0 Wonderful
Good flight, seated and had a water within 5 minutes. Crew was hospitable.
T
2.0 Poor
Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.
R
10.0 Wonderful
We arrived at DFW early!!
G
2.0 Poor
Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.
A
2.0 Poor
Flight delayed, poor internet
K
6.0 Okay
Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries
K
2.0 Poor
I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight
A
2.0 Poor
A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.
Read more about American Airlines

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Frontier flights to Chicago
Spirit Airlines flights to Chicago
Delta flights to Chicago
Southwest flights to Chicago
United Airlines flights to Chicago