CHI

Find cheap American Airlines flights to Chicago from $59

1 adult
1 adult, Economy

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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

Sat, Aug 30 - Tue, Sep 2
American Airlines Logo
5:40 pm - 7:34 pmBOS-ORD
2h 54mnonstop
American Airlines Logo
8:25 pm - 11:59 pmORD-BOS
2h 34mnonstop
$117American Airlines
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Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
7:24 pm - 9:21 pmBOS-ORD
2h 57mnonstop
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
$126American Airlines
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Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
8:35 am - 10:32 amBOS-ORD
2h 57mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$127American Airlines
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Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
3:00 pm - 5:03 pmBOS-ORD
3h 03mnonstop
American Airlines Logo
7:00 am - 10:24 amORD-BOS
2h 24mnonstop
$128American Airlines
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Tue, Jul 29 - Tue, Jul 29
American Airlines Logo
5:00 am - 6:58 amBOS-ORD
2h 58mnonstop
American Airlines Logo
9:55 am - 1:18 pmORD-BOS
2h 23mnonstop
$132American Airlines
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Thu, Sep 11 - Sat, Sep 20
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
American Airlines Logo
6:05 am - 9:32 amORD-BOS
2h 27mnonstop
$137American Airlines
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Tue, Jul 29 - Wed, Jul 30
American Airlines Logo
5:00 am - 6:58 amBOS-ORD
2h 58mnonstop
American Airlines Logo
6:25 am - 9:49 amORD-BOS
2h 24mnonstop
$138American Airlines
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Tue, Aug 12 - Tue, Aug 19
American Airlines Logo
5:28 am - 7:24 amBOS-ORD
2h 56mnonstop
American Airlines Logo
7:00 am - 10:24 amORD-BOS
2h 24mnonstop
$140American Airlines
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Wed, Sep 3 - Wed, Sep 10
American Airlines Logo
7:30 am - 9:10 amJFK-ORD
2h 40mnonstop
American Airlines Logo
1:59 pm - 5:17 pmORD-JFK
2h 18mnonstop
$142American Airlines
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Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
5:45 am - 7:23 amLGA-ORD
2h 38mnonstop
American Airlines Logo
7:00 pm - 10:19 pmORD-LGA
2h 19mnonstop
$142American Airlines
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Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$59
Average price round-trip$236
Good deal one-way$1,118
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 7% 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, Allegiant Air, Frontier, Alaska Airlines, Contour, Frontier, Delta, Avelo Airlines, Spirit Airlines and Denver Air Connection.

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

    On average, American Airlines flights to Chicago cost $330 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 Valparaiso and cost $85.

American Airlines customer reviews

7.2
GoodBased on 10,000 verified guest reviews
8.0Crew
7.5Boarding
6.9Entertainment
7.2Comfort
6.5Food
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
S
6.0 Okay
Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!
S
8.0 Very good
Comfortable seats - short flight
M
2.0 Poor
Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.
G
2.0 Poor
After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.
F
8.0 Very good
Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.
S
2.0 Poor
nearly 5 hour delay
A
10.0 Wonderful
Great
X
4.0 Mediocre
The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.
R
8.0 Very good
bro they actually gave us food
R
6.0 Okay
Food too small portion
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
Southwest flights to Chicago
Delta flights to Chicago

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