CHI

Find cheap American Airlines flights to Chicago from $59

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

Tue, Dec 9 - Tue, Dec 9
American Airlines Logo
7:00 am - 9:32 amBOS-ORD
3h 32mnonstop
American Airlines Logo
8:40 pm - 12:13 amORD-BOS
2h 33mnonstop
$117American Airlines
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Thu, Jan 8 - Sun, Jan 11
American Airlines Logo
8:00 pm - 10:18 pmDFW-ORD
2h 18mnonstop
American Airlines Logo
5:05 am - 7:47 amORD-DFW
2h 42mnonstop
$117American Airlines
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Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
8:00 pm - 10:18 pmDFW-ORD
2h 18mnonstop
American Airlines Logo
5:05 am - 7:47 amORD-DFW
2h 42mnonstop
$118American Airlines
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Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
6:15 am - 8:38 amDFW-ORD
2h 23mnonstop
American Airlines Logo
5:05 am - 7:47 amORD-DFW
2h 42mnonstop
$119American Airlines
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Fri, Dec 5 - Tue, Dec 9
American Airlines Logo
7:01 pm - 9:14 pmBOS-ORD
3h 13mnonstop
American Airlines Logo
1:17 pm - 4:52 pmORD-BOS
2h 35mnonstop
$122American Airlines
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Thu, Jan 1 - Mon, Jan 5
American Airlines Logo
6:36 am - 8:47 amBOS-ORD
3h 11mnonstop
American Airlines Logo
8:20 pm - 11:51 pmORD-BOS
2h 31mnonstop
$125American Airlines
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Fri, Dec 5 - Sun, Dec 7
American Airlines Logo
7:01 pm - 9:14 pmBOS-ORD
3h 13mnonstop
American Airlines Logo
6:10 am - 9:35 amORD-BOS
2h 25mnonstop
$127American Airlines
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Sun, Dec 14 - Thu, Dec 18
American Airlines Logo
6:00 am - 8:17 amBOS-ORD
3h 17mnonstop
American Airlines Logo
8:20 pm - 11:51 pmORD-BOS
2h 31mnonstop
$129American Airlines
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Thu, Dec 11 - Tue, Jan 6
American Airlines Logo
7:00 am - 9:32 amBOS-ORD
3h 32mnonstop
American Airlines Logo
7:00 am - 10:23 amORD-BOS
2h 23mnonstop
$132American Airlines
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Tue, Mar 3 - Tue, Mar 3
American Airlines Logo
11:59 am - 1:58 pmJFK-ORD
2h 59mnonstop
American Airlines Logo
4:25 pm - 7:45 pmORD-JFK
2h 20mnonstop
$134American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$59
Average price round-trip$289
Good deal one-way$2,371
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Dallas/Fort Worth 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, United Airlines, Southwest, Allegiant Air, Allegiant Air, Frontier, Contour, Denver Air Connection, Frontier, Delta, Alaska Airlines and Avelo Airlines.

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

    On average, American Airlines flights to Chicago cost $363 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 White Plains and cost $103.
  • 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
7.5Boarding
7.2Comfort
8.0Crew
6.4Food
6.9Entertainment
Pros +
Cons -
  • Time to start offering complimentary wifi in first class (in 135 reviews)
Show reviews that mention
Traveler rating:
Sort by:
L
6.0 Okay
Entertainment could have been better.
A
2.0 Poor
Qantas lost my baggage
R
10.0 Wonderful
Staff were kind and lovely. Food was lovely.
L
2.0 Poor
Bird strike caused return to PHL for plane changes
M
8.0 Very good
No upgrade
J
8.0 Very good
More choices on snacks. Built-in video screen to enjoy entertainment choices.
J
8.0 Very good
Better snacks. More movie choices.
K
10.0 Wonderful
Great!
A
6.0 Okay
we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.
A
6.0 Okay
flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.
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.
United Airlines flights to Chicago
Frontier flights to Chicago
Spirit Airlines flights to Chicago
Delta flights to Chicago