CHI

Find cheap American Airlines flights to Chicago from $68

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

Fri, May 29 - Sun, May 31
American Airlines Logo
6:00 am - 7:30 am
BWI
-
ORD
2h 30mnonstop
American Airlines Logo
6:56 am - 10:03 am
ORD
-
BWI
2h 07mnonstop
$115American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
8:29 am - 10:17 am
LGA
-
ORD
2h 48mnonstop
American Airlines Logo
8:55 am - 12:11 pm
ORD
-
LGA
2h 16mnonstop
$119American Airlines
Tue, Apr 14 - Sat, Apr 18
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
$123American Airlines
Tue, Apr 14 - Sat, Apr 18
American Airlines Logo
6:15 am - 8:50 am
DFW
-
ORD
2h 35mnonstop
American Airlines Logo
6:56 pm - 9:40 pm
ORD
-
DFW
2h 44mnonstop
$126American Airlines
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
6:38 am - 8:30 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
5:01 pm - 8:15 pm
ORD
-
LGA
2h 14mnonstop
$130American Airlines
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
6:38 am - 8:30 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
5:01 pm - 8:15 pm
ORD
-
LGA
2h 14mnonstop
$131American Airlines
Wed, Apr 8 - Sat, Apr 11
American Airlines Logo
7:32 pm - 10:00 pm
DFW
-
ORD
2h 28mnonstop
American Airlines Logo
8:45 pm - 11:23 pm
ORD
-
DFW
2h 38mnonstop
$132American Airlines
Mon, Apr 13 - Wed, Apr 15
American Airlines Logo
5:39 am - 7:11 am
BWI
-
ORD
2h 32mnonstop
American Airlines Logo
8:05 am - 11:11 am
ORD
-
BWI
2h 06mnonstop
$136American Airlines
Mon, Jul 6 - Sat, Jul 11
American Airlines Logo
7:08 am - 10:46 am
DEN
-
ORD
2h 38mnonstop
American Airlines Logo
10:20 pm - 12:07 am
ORD
-
DEN
2h 47mnonstop
$139American Airlines
Wed, Apr 22 - Wed, Apr 22
American Airlines Logo
12:10 pm - 2:13 pm
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
4:36 pm - 8:03 pm
ORD
-
JFK
2h 27mnonstop
$142American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Average price round-trip$275
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 Baltimore 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 Southwest, United Airlines, Allegiant Air, United Airlines, Frontier, Frontier, Avelo Airlines, Contour, 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 $317 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 $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 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
7.5Boarding
6.9Entertainment
8.0Crew
7.2Comfort
6.4Food
Traveler rating:
Sort by:
S
2.0 Poor
We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.
C
10.0 Wonderful
Very good
T
8.0 Very good
No Snacks or Entertainment. The flight was short, snacks should still be given.
S
2.0 Poor
We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.
J
10.0 Wonderful
See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.
J
4.0 Mediocre
American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.
K
6.0 Okay
Fine. Delayed slightly
K
8.0 Very good
It was good except my luggage was damaged!
A
10.0 Wonderful
Everything were good
D
6.0 Okay
The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.
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
Southwest flights to Chicago