CHI

Find cheap American Airlines flights to Chicago from $79

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

Fri, May 1 - Mon, May 4
American Airlines Logo
7:40 pm - 9:50 pm
BOS
-
ORD
3h 10mnonstop
American Airlines Logo
8:56 pm - 12:25 am
ORD
-
BOS
2h 29mnonstop
$157American Airlines
Sat, Apr 11 - Sun, Apr 12
American Airlines Logo
4:34 pm - 6:51 pm
BOS
-
ORD
3h 17mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$158American Airlines
Sat, Apr 11 - Sun, Apr 12
American Airlines Logo
5:35 pm - 7:52 pm
BOS
-
ORD
3h 17mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$159American Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$167American Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$168American Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$169American Airlines
Fri, Apr 10 - Sun, Apr 12
American Airlines Logo
7:40 pm - 9:50 pm
BOS
-
ORD
3h 10mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$170American Airlines
Tue, Apr 7 - Tue, Apr 7
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
3:16 pm - 6:50 pm
ORD
-
BOS
2h 34mnonstop
$177American Airlines
Thu, Apr 9 - Sun, Apr 12
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$178American Airlines
Sat, Apr 11 - Sun, Apr 12
American Airlines Logo
3:16 pm - 5:30 pm
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$179American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$79
Average price round-trip$345
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Boston 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, Contour, United Airlines, Frontier, Frontier, Alaska Airlines, Denver Air Connection, Delta and Allegiant Air.

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

    On average, American Airlines flights to Chicago cost $368 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 Manchester and cost $132.
  • 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

7.1
Good10,000 verified ratings
7.2Comfort
6.4Food
7.9Crew
7.5Boarding
6.9Entertainment
Traveler rating:
Sort by:
S
2.0 Poor
Very poor food. Took more than 90 minutes for baggage to arrive at DFW
L
10.0 Wonderful
British Airways is an excellent airline. Comfort, food and airline personnel.
L
10.0 Wonderful
British Airways is an excellent travel service. Comfort, food and airline personnel.
J
10.0 Wonderful
Good
S
2.0 Poor
Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.
S
2.0 Poor
Terrible planning. And even worse gate agents. Absolutely rude behavior.
J
2.0 Poor
Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.
J
8.0 Very good
Flight was delayed, gate was switched to another terminal.
J
2.0 Poor
Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.
R
4.0 Mediocre
Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent
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
United Airlines flights to Chicago
Delta flights to Chicago
Spirit Airlines flights to Chicago
Southwest flights to Chicago