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

Sat, Jan 31 - Sat, Feb 7
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
$118American Airlines
Tue, Feb 24 - Fri, Feb 27
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
$122American Airlines
Sun, Jan 18 - Tue, Jan 20
American Airlines Logo
8:59 am - 10:50 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
4:14 pm - 7:31 pm
ORD
-
JFK
2h 17mnonstop
$123American Airlines
Mon, Feb 23 - Wed, Feb 25
American Airlines Logo
3:59 pm - 6:00 pm
JFK
-
ORD
3h 01mnonstop
American Airlines Logo
4:10 pm - 7:29 pm
ORD
-
JFK
2h 19mnonstop
$127American Airlines
Fri, Feb 27 - Sun, Mar 1
American Airlines Logo
4:30 pm - 6:24 pm
LGA
-
ORD
2h 54mnonstop
American Airlines Logo
6:29 pm - 9:43 pm
ORD
-
LGA
2h 14mnonstop
$132American Airlines
Sat, Feb 14 - Sat, Feb 14
American Airlines Logo
5:17 pm - 6:42 pm
BWI
-
ORD
2h 25mnonstop
American Airlines Logo
8:30 pm - 11:29 pm
ORD
-
BWI
1h 59mnonstop
$134American Airlines
Wed, Mar 11 - Mon, Mar 16
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
$137American Airlines
Sat, Mar 14 - Sat, Mar 14
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
$137American Airlines
Fri, Mar 13 - Tue, Mar 17
American Airlines Logo
6:38 am - 8:30 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
7:23 am - 10:30 am
ORD
-
LGA
2h 07mnonstop
$137American Airlines
Thu, Feb 19 - Mon, Feb 23
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
$138American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$65
Average price round-trip$254
Good deal one-way$684
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New York LaGuardia 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, Frontier, Allegiant Air, Contour, United Airlines, Frontier, Delta, Avelo Airlines, Avelo Airlines, Denver Air Connection and Denver Air Connection.

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

    On average, American Airlines flights to Chicago cost $369 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 2 weeks 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 January.

American Airlines customer reviews

7.2
Good10,000 verified ratings
7.2Comfort
7.5Boarding
6.4Food
8.0Crew
6.9Entertainment
Traveler rating:
Sort by:
D
8.0 Very good
Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?
C
8.0 Very good
They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.
C
10.0 Wonderful
Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!
C
10.0 Wonderful
Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!
C
2.0 Poor
We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.
C
2.0 Poor
Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.
A
8.0 Very good
WiFi wasn’t working for the flight.
S
10.0 Wonderful
Excellent service and staff
T
4.0 Mediocre
It was on time
A
6.0 Okay
Prices are too high
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
Delta flights to Chicago
United Airlines flights to Chicago
Southwest flights to Chicago