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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

Tue, Jan 5 - Thu, Jan 14
American Airlines Logo
12:15 pm - 4:46 pmORD  Chicago O'Hare Intl-EYW Key West
3h 31mnonstop
American Airlines Logo
12:12 pm - 3:00 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 48mnonstop
$293American Airlines
Sat, Dec 5 - Wed, Dec 9
American Airlines Logo
10:31 am - 7:27 pmORD  Chicago O'Hare Intl-EYW Key West
7h 56m1 stop Miami
American Airlines Logo
1:01 pm - 3:50 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 49mnonstop
$303American Airlines
Sat, Dec 5 - Wed, Dec 9
American Airlines Logo
10:31 am - 7:27 pmORD  Chicago O'Hare Intl-EYW Key West
7h 56m1 stop Miami
American Airlines Logo
5:50 pm - 10:36 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 46m1 stop Charlotte Douglas
$313American Airlines
Sun, Nov 22 - Wed, Nov 25
American Airlines Logo
6:00 am - 9:52 amTPA  Tampa-EYW Key West
3h 52m1 stop Miami
American Airlines Logo
6:30 am - 10:50 amEYW  Key West-TPA Tampa
4h 20m1 stop Miami
$334American Airlines
Wed, Jan 20 - Sat, Jan 23
American Airlines Logo
6:00 am - 11:02 amCVG  Cincinnati Cinci./N. Kentucky-EYW Key West
5h 02m1 stop Miami
American Airlines Logo
8:06 pm - 12:39 amEYW  Key West-CVG Cincinnati Cinci./N. Kentucky
4h 33m1 stop Miami
$335American Airlines
Tue, Mar 2 - Tue, Mar 9
American Airlines Logo
7:00 am - 11:24 amORD  Chicago O'Hare Intl-EYW Key West
3h 24mnonstop
American Airlines Logo
6:15 pm - 9:10 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$336American Airlines
Sat, Nov 14 - Sat, Nov 21
American Airlines Logo
11:45 am - 4:27 pmTPA  Tampa-EYW Key West
4h 42m1 stop Miami
American Airlines Logo
7:37 pm - 12:09 amEYW  Key West-TPA Tampa
4h 32m1 stop Miami
$345American Airlines
Fri, Dec 4 - Thu, Dec 10
American Airlines Logo
6:56 am - 4:16 pmORD  Chicago O'Hare Intl-EYW Key West
8h 20m1 stop Miami
American Airlines Logo
5:16 pm - 8:09 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 53mnonstop
$346American Airlines
Sat, Nov 14 - Wed, Nov 18
American Airlines Logo
10:14 am - 4:27 pmORD  Chicago O'Hare Intl-EYW Key West
5h 13m1 stop Miami
American Airlines Logo
11:14 am - 6:23 pmEYW  Key West-ORD Chicago O'Hare Intl
8h 09m1 stop Miami
$356American Airlines
Mon, Dec 21 - Thu, Dec 24
American Airlines Logo
11:36 am - 2:52 pmDCA  Washington, D.C. Reagan-National-EYW Key West
3h 16mnonstop
American Airlines Logo
6:07 pm - 8:59 pmEYW  Key West-DCA Washington, D.C. Reagan-National
2h 52mnonstop
$359American 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 $385 (return) on average. On the other hand, the most expensive months to fly this route on American Airlines are March and April, where the average cost of round-trip tickets is $530 and $520 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 $157 one-way, and $293 round-trip on the route from Chicago O'Hare Intl Airport to Key West. The most popular route is from Tampa to Key West and the cheapest ticket found on this route in the last 5 days was $334 return.

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

Each week there are around 76 direct flights from within the United States to Key West. The most common day for departures is Monday, with 14% 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 $462. On the other hand, the most expensive day to fly is Sunday, where prices are $604 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 afternoon, when flights cost $460 on average.

Good to know

Low season

August

Cheapest flight

$157

Average price round-trip

$535

Good deal one-way

$550
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 2% 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 Delta, Allegiant Air, Breeze Airways, United Airlines, Allegiant Air and Delta.

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

    On average, American Airlines flights to Key West cost $429 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 New York LaGuardia Airport and cost $278.
  • 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

7.0
Good10,000 verified ratings
6.4Food
7.1Comfort
7.4Boarding
7.9Crew
6.8Entertainment
Traveler rating:
Sort by:
J
8.0 Very good
Flight was delayed a couple of times. Which is annoying, but manageable.
A
8.0 Very good
Too little snack and drink for almost 6:00 hr flight. Should have serve some food.
M
2.0 Poor
At 5:46 am EST, when I arrived at my departing gate, your gqte agent told me that I could not board the flight because the flight is closed 15 minuets before departure. However, the same gate agent escorted a woman (standing right next to me) at the gate onto the flight which, proves that I could have boarded the flight just like the woman I watched board the flight. The gate agent stated "she was here before you". 1-why was she not already on the flight & 2-how and why was she able to board a "closed" flight that I was not. Additionally, although 6am EST was the time of departure, the plane did not 'pullback' from the gate until 6:15am EST The same gate agent told me that the "boarding closes 15 before departure time" is printed on my boarding pass. This statement is not displayed on my digital boarding pass that I downloaded from AA.com. She also told me that this in stated on AA.com whent I booked my ticket however, since am travelling for work, I booked my flight thru my firm's (Deloitte Consulting) corporate travel app, not AA.com. Marc W Brown
S
10.0 Wonderful
What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.
S
10.0 Wonderful
Although it was a smaller plane, the flight was quick and uneventful.
S
2.0 Poor
This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.
S
2.0 Poor
This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.
T
10.0 Wonderful
Good
D
4.0 Mediocre
Same the delay was not ideal and the credits to move flights was not sufficient
D
4.0 Mediocre
The delay was not handled well and the offers to move flights and get travel credit was also not ideal.
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