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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
Tue, Jan 5 - Mon, Jan 11
American Airlines Logo
7:20 am - 11:51 amORD  Chicago O'Hare Intl-EYW Key West
3h 31mnonstop
American Airlines Logo
7:50 pm - 1:05 amEYW  Key West-ORD Chicago O'Hare Intl
6h 15m1 stop Miami
$303American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
7:00 am - 1:14 pmTPA  Tampa-EYW Key West
6h 14m1 stop Miami
American Airlines Logo
7:57 pm - 12:11 amEYW  Key West-TPA Tampa
4h 14m1 stop Miami
$305American Airlines
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
9:15 am - 5:19 pmORD  Chicago O'Hare Intl-EYW Key West
7h 04m1 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
Wed, Jan 20 - Mon, Jan 25
American Airlines Logo
7:00 am - 11:02 amTPA  Tampa-EYW Key West
4h 02m1 stop Miami
American Airlines Logo
7:50 pm - 11:21 pmEYW  Key West-TPA Tampa
3h 31m1 stop Miami
$334American Airlines
Tue, Feb 2 - Sat, Feb 6
American Airlines Logo
1:00 pm - 5:28 pmORD  Chicago O'Hare Intl-EYW Key West
3h 28mnonstop
American Airlines Logo
5:58 pm - 8:59 pmEYW  Key West-ORD Chicago O'Hare Intl
4h 01mnonstop
$336American Airlines
Tue, Apr 6 - Tue, Apr 13
American Airlines Logo
6:35 am - 1:21 pmPIT  Pittsburgh-EYW Key West
6h 46m1 stop Charlotte Douglas
American Airlines Logo
8:05 am - 2:40 pmEYW  Key West-PIT Pittsburgh
6h 35m1 stop Charlotte Douglas
$339American Airlines
Mon, Mar 1 - Wed, Mar 31
American Airlines Logo
8:11 am - 3:53 pmORD  Chicago O'Hare Intl-EYW Key West
6h 42m1 stop Charlotte Douglas
American Airlines Logo
6:15 pm - 9:10 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$346American Airlines
Mon, Mar 1 - Wed, Mar 31
American Airlines Logo
6:50 am - 3:53 pmORD  Chicago O'Hare Intl-EYW Key West
8h 03m1 stop Charlotte Douglas
American Airlines Logo
9:39 am - 3:50 pmEYW  Key West-ORD Chicago O'Hare Intl
7h 11m1 stop Miami
$356American Airlines
Thu, Feb 4 - Sun, Feb 7
American Airlines Logo
2:53 pm - 6:08 pmDCA  Washington, D.C. Reagan-National-EYW Key West
3h 15mnonstop
American Airlines Logo
6:48 pm - 9:31 pmEYW  Key West-DCA Washington, D.C. Reagan-National
2h 43mnonstop
$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 $388 (return) on average. On the other hand, the most expensive months to fly this route on American Airlines are March and November, where the average cost of round-trip tickets is $532 and $522 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 $190 one-way, and $397 round-trip on the route from Boston 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 $305 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

$190

Average price round-trip

$536

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 Boston 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
7.9Crew
6.8Entertainment
6.4Food
7.4Boarding
7.1Comfort
Traveler rating:
Sort by:
M
10.0 Wonderful
Good Upgrade
A
6.0 Okay
It routinely takes 45-50 minutes to gat luggage at CLT
S
2.0 Poor
The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.
A
10.0 Wonderful
excellent.
N
2.0 Poor
Both flights delayed without any reason
G
4.0 Mediocre
I didn't like anything about this flight. The only reason anyone drinks Jack is because you ran out of Woodford. You should know to stock more Woodford. When you wait of first class hand and foot from the minute they get on the plane 5 feet from me but then start service from the rear of the plane so main cabin plus gets the scraps, that's how you get people to stop flying your airline.
A
2.0 Poor
American Airlines was horrible! The layover flight to DFW was delayed with no clear communication and for us having to stay the whole day which led to staying a night in Dallas was comped with 2 $12 dollar vouchers and a crappy hotel. We missed a whole day in Tokyo for our honeymoon and stressed the whole 24 hours. We were supposed to leave at the same time the following day, but that was delayed hours again. And instead of letting the delayed flight go first, they let the flight that was scheduled ahead of us. American should refund us the day wasted in Dallas that should have been in Tokyo! We had lost out on paid events that we can’t get refunded. When we finally did leave, it was a good flight. You would think that was the only issue with American but we from the LAX layover, we were delayed 6 hours and were given a $12 dollar voucher that covered a drink only. The only communication we were given then was that because they were delayed in a prior flight we were delayed again. I don’t understand why it was only with American that we had such a bad time with! They have definitely left a sour taste in our mouths for our honeymoon! And then they did send an email saying we could have 2K miles…. For what? To be delayed into another day and miss our flight again?
M
4.0 Mediocre
The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.
A
2.0 Poor
Flight was dirty and delayed by an hour
A
2.0 Poor
It was delayed by 45 minutes
Read more about American Airlines

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