CHI

Find cheap American Airlines flights to Chicago from $65

1 adult
1 adult, Economy, 0 bags

Search hundreds of travel sites at once for deals on American Airlines flights to Chicago

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
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

Thu, Jan 22 - Sun, Jan 25
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
4:14 pm - 7:31 pm
ORD
-
JFK
2h 17mnonstop
$97American Airlines
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
11:40 am - 2:54 pm
ORD
-
JFK
2h 14mnonstop
$98American Airlines
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
4:14 pm - 7:31 pm
ORD
-
JFK
2h 17mnonstop
$99American Airlines
Mon, Feb 2 - Wed, Feb 4
American Airlines Logo
12:30 pm - 2:29 pm
JFK
-
ORD
2h 59mnonstop
American Airlines Logo
8:16 am - 11:39 am
ORD
-
JFK
2h 23mnonstop
$108American Airlines
Mon, Feb 2 - Thu, Feb 5
American Airlines Logo
12:30 pm - 2:29 pm
JFK
-
ORD
2h 59mnonstop
American Airlines Logo
4:14 pm - 7:31 pm
ORD
-
JFK
2h 17mnonstop
$113American Airlines
Wed, Jan 21 - Thu, Jan 22
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
11:44 am - 2:58 pm
ORD
-
JFK
2h 14mnonstop
$115American Airlines
Mon, Feb 2 - Wed, Feb 18
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
7:45 am - 11:11 am
ORD
-
JFK
2h 26mnonstop
$117American Airlines
Thu, Feb 26 - Mon, Mar 2
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
$118American Airlines
Wed, Jan 28 - Sat, Jan 31
American Airlines Logo
3:44 pm - 5:47 pm
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
8:16 am - 11:39 am
ORD
-
JFK
2h 23mnonstop
$119American Airlines
Sat, Feb 7 - Sat, Feb 14
American Airlines Logo
3:44 pm - 5:47 pm
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
7:45 am - 11:11 am
ORD
-
JFK
2h 26mnonstop
$120American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$65
Average price round-trip$338
Best time to beat the crowds with an average 13% 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, Frontier, Contour, Denver Air Connection, United Airlines, Frontier, Delta, Avelo Airlines and Avelo Airlines.

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

    On average, American Airlines flights to Chicago cost $379 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?

    Unfortunately, there are no other airlines in oneworld that fly to Chicago.

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 $69.
  • If you’re intending to fly with American Airlines, book your flight to Chicago at least 1 week before departure to ensure a below-average price.
  • High season for flights to Chicago with American Airlines is May and prices are highest at this time. The cheapest month to fly is February.

American Airlines customer reviews

7.2
Good10,000 verified ratings
6.9Entertainment
7.2Comfort
7.5Boarding
8.0Crew
6.4Food
Show reviews that mention
Traveler rating:
Sort by:
A
10.0 Wonderful
The flight was very smooth and the meal in business class was great.
A
10.0 Wonderful
The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.
A
8.0 Very good
I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.
K
4.0 Mediocre
Seat 19d had a broken and tilted table
R
6.0 Okay
Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.
K
8.0 Very good
Better service. No food options, but we did get drinks and a cookie.
K
8.0 Very good
Boarding was organized and timely. Food was mediocre, especially for first class travel.
J
2.0 Poor
the flight was 4 hours late
L
6.0 Okay
Delayed, turbulent, other than that good
E
2.0 Poor
We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.
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
United Airlines flights to Chicago
Delta flights to Chicago