CHI

Find cheap American Airlines flights to Chicago from $59

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 23% 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

Wed, Feb 18 - Wed, Feb 25
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
$117American Airlines
Sat, Feb 7 - Tue, Feb 10
American Airlines Logo
5:59 pm - 7:49 pm
EWR
-
ORD
2h 50mnonstop
American Airlines Logo
7:49 pm - 10:59 pm
ORD
-
EWR
2h 10mnonstop
$117American Airlines
Thu, Feb 12 - Sun, Feb 15
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
$117American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
11:59 am - 1:56 pm
JFK
-
ORD
2h 57mnonstop
American Airlines Logo
4:10 pm - 7:29 pm
ORD
-
JFK
2h 19mnonstop
$126American Airlines
Sat, Feb 21 - Tue, Feb 24
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
$126American Airlines
Tue, Mar 17 - Tue, Mar 31
American Airlines Logo
8:59 am - 10:56 am
JFK
-
ORD
2h 57mnonstop
American Airlines Logo
4:21 pm - 7:40 pm
ORD
-
JFK
2h 19mnonstop
$127American Airlines
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
6:38 am - 8:30 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
8:49 pm - 11:59 pm
ORD
-
LGA
2h 10mnonstop
$127American Airlines
Mon, Feb 23 - Wed, Mar 4
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
$132American Airlines
Fri, Feb 20 - Tue, Feb 24
American Airlines Logo
8:29 am - 10:26 am
JFK
-
ORD
2h 57mnonstop
American Airlines Logo
7:45 am - 11:11 am
ORD
-
JFK
2h 26mnonstop
$136American Airlines
Tue, Feb 24 - Tue, Mar 3
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
$137American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$59
Average price round-trip$279
Good deal one-way$595
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Newark Liberty 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, Allegiant Air, Contour, Frontier, Frontier, Denver Air Connection, Denver Air Connection, Delta, United Airlines and Alaska Airlines.

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

    On average, American Airlines flights to Chicago cost $331 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 $88.
  • 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 December.

American Airlines customer reviews

7.2
Good10,000 verified ratings
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
8.0Crew
Traveler rating:
Sort by:
S
8.0 Very good
The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.
R
10.0 Wonderful
Excellent
R
10.0 Wonderful
We were upgraded to Business Class. So comfortable with great service and food options
C
2.0 Poor
Flight cancelled, never rebooked Had to use another airline
M
2.0 Poor
The flight attendant use 1.5 hours to answer my call. My dirty food tray was unattended.
R
6.0 Okay
My flight to London from Philadelphia was cancelled due to weather.
R
10.0 Wonderful
The attendants were kind and helpful. A sugar-free drink would have been very welcome.
A
10.0 Wonderful
Pilot navigated severe weather/snow storm with skill. Described his intentions clearly
C
10.0 Wonderful
Crew was great.
A
8.0 Very good
one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather
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.
Spirit Airlines flights to Chicago
Frontier flights to Chicago
United Airlines flights to Chicago
Delta flights to Chicago