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Flight Deals

Cheap American Airlines Flight Deals to Key West

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip American Airlines flight deals to Key West

Wed, Jan 20 - Sat, Jan 23
American Airlines Logo
5:08 pm - 9:47 pmCVG  Cincinnati Cinci./N. Kentucky-EYW Key West
4h 39m1 stop Charlotte Douglas
American Airlines Logo
12:00 pm - 5:38 pmEYW  Key West-CVG Cincinnati Cinci./N. Kentucky
5h 38m1 stop Miami
$295American Airlines
Sat, Dec 5 - Thu, Dec 10
American Airlines Logo
7:29 am - 11:53 amORD  Chicago O'Hare Intl-EYW Key West
3h 24mnonstop
American Airlines Logo
1:14 pm - 4:00 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 46mnonstop
$319American Airlines
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
12:20 pm - 7:33 pmEWR  Newark-EYW Key West
7h 13m1 stop Miami
American Airlines Logo
6:35 pm - 12:59 amEYW  Key West-EWR Newark
6h 24m1 stop Miami
$319American Airlines
Wed, Jan 20 - Tue, Jan 26
American Airlines Logo
10:06 am - 2:06 pmLGA  New York LaGuardia-EYW Key West
4h 00mnonstop
American Airlines Logo
2:44 pm - 5:59 pmEYW  Key West-LGA New York LaGuardia
3h 15mnonstop
$319American Airlines
Wed, Sep 23 - Tue, Sep 29
American Airlines Logo
10:05 am - 7:17 pmORD  Chicago O'Hare Intl-EYW Key West
8h 12m1 stop Miami
American Airlines Logo
1:47 pm - 6:07 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 20m1 stop Miami
$323American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
6:00 am - 10:44 amBWI  Baltimore/Washington-EYW Key West
4h 44m1 stop Miami
American Airlines Logo
10:18 am - 3:15 pmEYW  Key West-BWI Baltimore/Washington
4h 57m1 stop Miami
$329American Airlines
Sat, Dec 5 - Sun, Dec 13
American Airlines Logo
8:05 am - 3:26 pmORD  Chicago O'Hare Intl-EYW Key West
6h 21m1 stop Charlotte Douglas
American Airlines Logo
5:05 pm - 8:00 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$329American Airlines
Fri, Oct 30 - Tue, Nov 3
American Airlines Logo
5:55 am - 1:03 pmLGA  New York LaGuardia-EYW Key West
7h 08m1 stop Miami
American Airlines Logo
2:25 pm - 5:48 pmEYW  Key West-LGA New York LaGuardia
3h 23mnonstop
$329American Airlines
Fri, Nov 13 - Mon, Nov 16
American Airlines Logo
12:15 pm - 4:37 pmORD  Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
American Airlines Logo
6:26 pm - 12:01 amEYW  Key West-ORD Chicago O'Hare Intl
6h 35m1 stop Charlotte Douglas
$330American Airlines
Wed, Sep 16 - Wed, Sep 23
American Airlines Logo
6:29 am - 1:11 pmORD  Chicago O'Hare Intl-EYW Key West
5h 42m1 stop Charlotte Douglas
American Airlines Logo
11:30 am - 6:07 pmEYW  Key West-ORD Chicago O'Hare Intl
7h 37m1 stop Miami
$331American Airlines
Useful Info

KAYAK's insights & trends for Key West flights with American Airlines

Get data-powered insights and trends into American Airlines flights to Key West to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly with American Airlines to Key West?

The cheapest month for American Airlines flights to Key West is January, where tickets cost $373 (return) on average. On the other hand, the most expensive months to fly this route on American Airlines are April and March, where the average cost of round-trip tickets is $524 and $523 respectively.

How far in advance should I book American Airlines flights to Key West?

For the absolute cheapest price on American Airlines, our data suggests you should book 5 weeks before departure.

What is the cheapest flight to Key West with American Airlines?

The cheapest airline ticket to Key West from the United States with American Airlines in the last 5 days was $162 one-way, and $319 round-trip on the route from Chicago O'Hare Intl Airport to Key West. The most popular route is from Baltimore to Key West and the cheapest ticket found on this route in the last 5 days was $329 return.

How many direct flights does American Airlines operate to Key West every week?

Each week there are around 65 direct flights from within the United States to Key West. The most common day for departures is Saturday, with 17% of flights taking off on this day.

What is the cheapest day to fly to Key West?

Based on KAYAK data, the cheapest day to fly to Key West is Tuesday where tickets can be as cheap as $476. On the other hand, the most expensive day to fly is Sunday, where prices are $593 on average.

What is the cheapest time of day to fly to Key West with American Airlines?

The cheapest time of day to fly to Key West with American Airlines is generally in the evening, when flights cost $467 on average.

Good to know

Low season

August

Cheapest flight

$162

Average price round-trip

$486

Good deal one-way

$295
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to Key West
(avg. price over the last 2 weeks)
or less

When to book flights with American Airlines to Key West

Average price per month
Flight prices as travel date approaches

FAQs for flying to Key West with American Airlines

  • Which other airlines fly to Key West?

    Along with American Airlines, you can also fly to Key West with Allegiant Air, Breeze Airways, Delta, United Airlines, Allegiant Air, Delta and United Airlines.

  • How much is a flight to Key West with American Airlines?

    On average, American Airlines flights to Key West cost $335 one-way.

  • Which airport do American Airlines flights to Key West fly into?

    You’ll fly into Key West when flying to Key West with American Airlines.

  • Are there any other airlines in oneworld that fly to Key West?

    Unfortunately, there are no other airlines in oneworld that fly to Key West.

Top tips for your flights to Key West with American Airlines

  • The cheapest flight to Key West with American Airlines found on KAYAK in the last 2 weeks departed from Miami and cost $243.
  • If you’re intending to fly with American Airlines, book your flight to Key West at least 1 week before departure to ensure a below-average price.
  • High season for flights to Key West with American Airlines is February and prices are highest at this time. The cheapest month to fly is August.

American Airlines customer reviews

7.1
Good10,000 verified ratings
7.9Crew
6.4Food
7.2Comfort
6.8Entertainment
7.5Boarding
Traveler rating:
Sort by:
T
10.0 Wonderful
Everything
A
10.0 Wonderful
Excellent
A
10.0 Wonderful
Excellent
A
10.0 Wonderful
Much better than Delta
B
10.0 Wonderful
awesome!
C
4.0 Mediocre
To many flight at the same hour...no respect to handicap....
A
4.0 Mediocre
The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.
M
6.0 Okay
DCA-LAX No screen on a 5 hour flight (almost) no food for sale on a 5 hour flight (practically) no wifi coverage or speed on a 5 hour flight I should have gotten my money back, shame on American
K
2.0 Poor
Delayed flight led to missed connection which led to new flight with 3 hours of delay so our family of 5 went from a 7pm arrival time to 1am Absolutely terrible yet again.
A
8.0 Very good
Flight was good, little delayed because of busy plane traffic
Read more about American Airlines

Everything you need to know for your flight to Key West

Other airlines flying to Key West

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United Airlines flights to Key West
Delta flights to Key West