CHI

Find cheap American Airlines flights to Chicago from $64

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

Thu, Jan 1 - Sat, Jan 31
American Airlines Logo
6:36 am - 8:47 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
8:18 pm - 11:44 pm
ORD
-
BOS
2h 26mnonstop
$132American Airlines
Wed, Jan 28 - Wed, Jan 28
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
$134American Airlines
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
6:00 am - 7:23 am
ATL
-
ORD
2h 23mnonstop
American Airlines Logo
4:04 pm - 7:07 pm
ORD
-
ATL
2h 03mnonstop
$137American Airlines
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
4:20 pm - 6:42 pm
BOS
-
ORD
3h 22mnonstop
American Airlines Logo
7:00 am - 10:23 am
ORD
-
BOS
2h 23mnonstop
$137American Airlines
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
8:16 am - 11:39 am
ORD
-
JFK
2h 23mnonstop
$139American Airlines
Sun, Jan 18 - Tue, Jan 20
American Airlines Logo
7:00 am - 8:53 am
EWR
-
ORD
2h 53mnonstop
American Airlines Logo
8:07 am - 11:23 am
ORD
-
EWR
2h 16mnonstop
$139American Airlines
Tue, Jan 13 - Tue, Jan 20
American Airlines Logo
6:59 am - 8:50 am
LGA
-
ORD
2h 51mnonstop
American Airlines Logo
1:45 pm - 5:02 pm
ORD
-
LGA
2h 17mnonstop
$139American Airlines
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
9:00 am - 10:51 am
JFK
-
ORD
2h 51mnonstop
American Airlines Logo
8:16 am - 11:39 am
ORD
-
JFK
2h 23mnonstop
$140American Airlines
Sun, Jan 18 - Tue, Jan 20
American Airlines Logo
7:00 am - 8:53 am
EWR
-
ORD
2h 53mnonstop
American Airlines Logo
8:07 am - 11:23 am
ORD
-
EWR
2h 16mnonstop
$140American Airlines
Thu, Jan 15 - Mon, Jan 19
American Airlines Logo
2:15 pm - 4:09 pm
LGA
-
ORD
2h 54mnonstop
American Airlines Logo
8:50 pm - 11:58 pm
ORD
-
LGA
2h 08mnonstop
$140American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Average price round-trip$335
Good deal one-way$464
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 Boston 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, Denver Air Connection, Frontier, Delta, Avelo Airlines, Avelo Airlines and Alaska Airlines.

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

    On average, American Airlines flights to Chicago cost $387 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 Marquette and cost $104.
  • 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
8.0Crew
7.2Comfort
6.5Food
7.5Boarding
Pros +
  • Flight crew was pleasant enough. (in 437 reviews)
  • Crew was good and mostly attentive (in 1650 reviews)
Cons -
Show reviews that mention
Traveler rating:
Sort by:
M
8.0 Very good
Great
M
6.0 Okay
Flight was late and boarding was confusing because gate changed and I didn’t get a notification
M
10.0 Wonderful
Great
A
8.0 Very good
Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.
A
6.0 Okay
The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.
C
6.0 Okay
Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.
F
8.0 Very good
A little delay to take off
A
10.0 Wonderful
No problems and on time
J
2.0 Poor
Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative
A
8.0 Very good
Quick and efficient boarding
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