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, Jun 13 - Tue, Jun 16
American Airlines Logo
9:59 am - 11:51 am
JFK
-
ORD
2h 52mnonstop
American Airlines Logo
4:33 pm - 8:04 pm
ORD
-
JFK
2h 31mnonstop
$177American Airlines
Thu, Jun 25 - Sat, Jun 27
American Airlines Logo
5:30 am - 7:18 am
EWR
-
ORD
2h 48mnonstop
American Airlines Logo
6:51 am - 10:02 am
ORD
-
EWR
2h 11mnonstop
$177American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
7:18 am - 9:05 am
LGA
-
ORD
2h 47mnonstop
American Airlines Logo
7:00 am - 10:10 am
ORD
-
LGA
2h 10mnonstop
$177American Airlines
Tue, Jul 21 - Thu, Jul 23
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 21 - Wed, Jul 22
American Airlines Logo
10:00 am - 11:47 am
LGA
-
ORD
2h 47mnonstop
American Airlines Logo
11:15 am - 2:29 pm
ORD
-
LGA
2h 14mnonstop
$178American Airlines
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
9:59 am - 11:51 am
JFK
-
ORD
2h 52mnonstop
American Airlines Logo
4:33 pm - 8:04 pm
ORD
-
JFK
2h 31mnonstop
$179American Airlines
Thu, Jun 25 - Thu, Aug 13
American Airlines Logo
5:30 am - 7:18 am
EWR
-
ORD
2h 48mnonstop
American Airlines Logo
8:30 pm - 11:59 pm
ORD
-
EWR
2h 29mnonstop
$179American Airlines
Tue, Jul 21 - Thu, Jul 23
American Airlines Logo
7:23 am - 9:10 am
LGA
-
ORD
2h 47mnonstop
American Airlines Logo
8:23 pm - 11:40 pm
ORD
-
LGA
2h 17mnonstop
$179American Airlines
Thu, Jun 25 - Thu, Aug 13
American Airlines Logo
5:30 am - 7:18 am
EWR
-
ORD
2h 48mnonstop
American Airlines Logo
8:30 pm - 11:59 pm
ORD
-
EWR
2h 29mnonstop
$181American Airlines
Tue, Jun 9 - Sat, Jun 13
American Airlines Logo
1:59 pm - 3:55 pm
JFK
-
ORD
2h 56mnonstop
American Airlines Logo
4:44 pm - 8:15 pm
ORD
-
JFK
2h 31mnonstop
$182American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$88
Average price round-trip$299
Best time to beat the crowds with an average 7% 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, Avelo Airlines, Denver Air Connection, Contour, Allegiant Air and Alaska Airlines.

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

    On average, American Airlines flights to Chicago cost $373 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
6.4Food
7.5Boarding
7.9Crew
Traveler rating:
Sort by:
L
8.0 Very good
AA was a very good experience. The employees are wonderful
A
2.0 Poor
Flight was 3 hours delayed. They gave our plan to two other routes. Need to knock that off.
N
2.0 Poor
To have arrived on time and not 3 hours late after having already spent $100 to change to an earlier flight, only to arrive back home close to the original flight time.
B
4.0 Mediocre
No lounge in dtw
D
4.0 Mediocre
No gate in Rome. Had stairs. Got separated from my wife in a wheel chair. Customs was a zoo. If AA doesnt have landing rights, it should be advertised.
A
10.0 Wonderful
I almost missed my flight and they helped me out enormously
D
10.0 Wonderful
Business class was very good, one of my best flights
P
2.0 Poor
The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.
P
6.0 Okay
The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!
L
10.0 Wonderful
The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

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.