CHI

Find cheap American Airlines flights to Chicago from $74

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

Wed, May 13 - Sat, May 16
American Airlines Logo
9:03 am - 10:58 am
JFK
-
ORD
2h 55mnonstop
American Airlines Logo
4:27 pm - 7:59 pm
ORD
-
JFK
2h 32mnonstop
$147American Airlines
Sat, May 23 - Wed, May 27
American Airlines Logo
2:20 pm - 4:10 pm
EWR
-
ORD
2h 50mnonstop
American Airlines Logo
6:50 am - 10:02 am
ORD
-
EWR
2h 12mnonstop
$147American Airlines
Thu, Apr 16 - Sun, Apr 19
American Airlines Logo
7:29 am - 9:22 am
LGA
-
ORD
2h 53mnonstop
American Airlines Logo
6:00 am - 9:12 am
ORD
-
LGA
2h 12mnonstop
$147American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
5:20 pm - 7:20 pm
EWR
-
ORD
3h 00mnonstop
American Airlines Logo
7:07 am - 10:28 am
ORD
-
EWR
2h 21mnonstop
$148American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
6:35 am - 8:25 am
EWR
-
ORD
2h 50mnonstop
American Airlines Logo
1:07 pm - 4:30 pm
ORD
-
EWR
2h 23mnonstop
$149American Airlines
Wed, Apr 1 - Mon, Apr 6
American Airlines Logo
7:23 am - 9:15 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
8:49 pm - 11:59 pm
ORD
-
LGA
2h 10mnonstop
$152American Airlines
Tue, Mar 31 - Mon, Apr 6
American Airlines Logo
9:00 am - 10:57 am
JFK
-
ORD
2h 57mnonstop
American Airlines Logo
4:21 pm - 7:40 pm
ORD
-
JFK
2h 19mnonstop
$155American Airlines
Fri, Mar 6 - Fri, Mar 6
American Airlines Logo
8:29 am - 10:26 am
JFK
-
ORD
2h 57mnonstop
American Airlines Logo
4:10 pm - 7:29 pm
ORD
-
JFK
2h 19mnonstop
$157American Airlines
Sun, Mar 8 - Tue, Mar 10
American Airlines Logo
7:10 am - 8:57 am
EWR
-
ORD
2h 47mnonstop
American Airlines Logo
6:47 pm - 10:08 pm
ORD
-
EWR
2h 21mnonstop
$157American Airlines
Fri, Mar 6 - Mon, Mar 9
American Airlines Logo
6:38 am - 8:30 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
2:51 pm - 5:59 pm
ORD
-
LGA
2h 08mnonstop
$157American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$74
Average price round-trip$265
Good deal one-way$672
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less

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, United Airlines, Allegiant Air, Contour, Frontier, Frontier, Avelo Airlines, Denver Air Connection, Delta and Alaska Airlines.

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

    On average, American Airlines flights to Chicago cost $313 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 Chicago Greater Rockford Airport and cost $95.
  • 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

7.2
Good10,000 verified ratings
7.2Comfort
7.5Boarding
8.0Crew
6.9Entertainment
6.4Food
Traveler rating:
Sort by:
D
8.0 Very good
I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.
C
8.0 Very good
The flight was fine, once we got underway. It was more than hour delayed
S
6.0 Okay
Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.
D
6.0 Okay
Waited for oxygen tanks for 30 minutes after boarding was complete.
V
4.0 Mediocre
Delayed flight, spotty internet,
A
2.0 Poor
The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.
A
2.0 Poor
The gates should be ready when we land. Waiting on the runway for a hour is ridiculous.
L
4.0 Mediocre
flight delayed, gate was changed.
G
8.0 Very good
The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.
A
10.0 Wonderful
It was great and swift no issues

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.