CHI

Find cheap American Airlines flights to Chicago from $68

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

Wed, Feb 18 - Wed, Feb 18
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
$134American Airlines
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
7:00 am - 9:05 am
BOS
-
ORD
3h 05mnonstop
American Airlines Logo
5:25 pm - 8:45 pm
ORD
-
BOS
2h 20mnonstop
$135American Airlines
Sat, Feb 28 - Mon, Mar 2
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
$137American Airlines
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
1:59 pm - 3:43 pm
EWR
-
ORD
2h 44mnonstop
American Airlines Logo
6:47 pm - 10:08 pm
ORD
-
EWR
2h 21mnonstop
$137American Airlines
Fri, Feb 27 - Sun, Mar 1
American Airlines Logo
8:10 pm - 10:02 pm
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
7:23 am - 10:30 am
ORD
-
LGA
2h 07mnonstop
$137American Airlines
Mon, Feb 23 - 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
$138American Airlines
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
1:15 pm - 3:14 pm
LGA
-
ORD
2h 59mnonstop
American Airlines Logo
11:55 am - 3:04 pm
ORD
-
LGA
2h 09mnonstop
$138American Airlines
Thu, Feb 12 - Tue, Feb 17
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
$139American Airlines
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
7:23 am - 9:15 am
LGA
-
ORD
2h 52mnonstop
American Airlines Logo
6:29 pm - 9:43 pm
ORD
-
LGA
2h 14mnonstop
$139American Airlines
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
5:00 am - 6:30 am
BWI
-
ORD
2h 30mnonstop
American Airlines Logo
8:30 pm - 11:33 pm
ORD
-
BWI
2h 03mnonstop
$139American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Average price round-trip$270
Good deal one-way$929
Best time to beat the crowds with an average 2% 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, Frontier, Allegiant Air, Contour, United Airlines, Frontier, Delta, Avelo Airlines, JetBlue, Denver Air Connection, Denver Air Connection and Spirit Airlines.

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

    On average, American Airlines flights to Chicago cost $349 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 $78.
  • 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
8.0Crew
6.9Entertainment
7.5Boarding
6.4Food
7.2Comfort
Traveler rating:
Sort by:
S
2.0 Poor
Multiple delays and gate changes
E
2.0 Poor
Delayed for preventable reasons (maintenance papers not filed correctly)
K
10.0 Wonderful
The professionals have excellent customer service, the seats don´t have enough space.
E
10.0 Wonderful
We were upgraded to First Class and it was a great flight
R
10.0 Wonderful
Amazing I love American. I’ll never fly anyone else if I can help it.
R
10.0 Wonderful
I love American. I’ll never fly anyone else if I can help it.
T
2.0 Poor
Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.
A
6.0 Okay
American Airlines sucks
A
4.0 Mediocre
American Airlines sucks
A
10.0 Wonderful
Great
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