Flight Deals
Cheap American Airlines Flight Deals to Key West
Here are some of the best deals found on KAYAK recently from American Airlines to Key West 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 Key West
Mon, Nov 2 - Wed, Nov 11
12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$292American Airlines
Mon, Nov 2 - Wed, Nov 11
12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$293American Airlines
Mon, Nov 2 - Wed, Nov 11
8:05 am - 3:06 pmORD Chicago O'Hare Intl-EYW Key West
6h 01m1 stop Charlotte Douglas
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$302American Airlines
Sat, Nov 14 - Wed, Nov 18
8:15 am - 4:27 pmORD Chicago O'Hare Intl-EYW Key West
7h 12m1 stop Miami
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$303American Airlines
Mon, Nov 2 - Wed, Nov 11
6:41 am - 1:03 pmORD Chicago O'Hare Intl-EYW Key West
5h 22m1 stop Charlotte Douglas
5:50 pm - 10:30 pmEYW Key West-ORD Chicago O'Hare Intl
5h 40m1 stop Charlotte Douglas
$311American Airlines
Sat, Nov 14 - Wed, Nov 18
10:14 am - 4:27 pmORD Chicago O'Hare Intl-EYW Key West
5h 13m1 stop Miami
11:14 am - 6:23 pmEYW Key West-ORD Chicago O'Hare Intl
8h 09m1 stop Miami
$313American Airlines
Sat, Nov 14 - Wed, Nov 18
11:49 am - 4:15 pmORD Chicago O'Hare Intl-EYW Key West
3h 26mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$326American Airlines
Fri, Nov 13 - Mon, Nov 16
12:15 pm - 4:37 pmORD Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
7:57 pm - 12:44 amEYW Key West-ORD Chicago O'Hare Intl
5h 47m1 stop Miami
$336American Airlines
Tue, Nov 17 - Sat, Nov 21
3:15 pm - 6:25 pmDCA Washington, D.C. Reagan-National-EYW Key West
3h 10mnonstop
5:28 pm - 8:18 pmEYW Key West-DCA Washington, D.C. Reagan-National
2h 50mnonstop
$339American Airlines
Wed, Dec 2 - Sun, Dec 6
8:10 am - 5:21 pmORD Chicago O'Hare Intl-EYW Key West
8h 11m1 stop Charlotte Douglas
8:00 pm - 12:53 amEYW Key West-ORD Chicago O'Hare Intl
5h 53m1 stop Miami
$346American Airlines
Recent one-way American Airlines flight deals to Key West
Wed, Nov 11
10:19 am - 6:25 pmBOS Boston Logan Intl-EYW Key West
8h 06m1 stop Washington, D.C. Reagan-National
$194American Airlines
Tue, Dec 8
3:15 pm - 6:27 pmDCA Washington, D.C. Reagan-National-EYW Key West
3h 12mnonstop
$204American Airlines
Sun, Dec 20
9:09 am - 1:28 pmBOS Boston Logan Intl-EYW Key West
4h 19mnonstop
$204American Airlines
Tue, Dec 8
5:00 am - 9:44 amDCA Washington, D.C. Reagan-National-EYW Key West
4h 44m1 stop Miami
$214American Airlines
Fri, Nov 20
12:29 pm - 6:53 pmEWR Newark-EYW Key West
6h 24m1 stop Miami
$214American Airlines
Thu, Oct 29
8:07 am - 1:54 pmBOS Boston Logan Intl-EYW Key West
5h 47m1 stop Philadelphia
$214American Airlines
Mon, Nov 9
12:26 pm - 7:02 pmEWR Newark-EYW Key West
6h 36m1 stop Miami
$215American Airlines
Wed, Dec 23
9:09 am - 1:28 pmBOS Boston Logan Intl-EYW Key West
4h 19mnonstop
$219American Airlines
Thu, Dec 17
9:28 am - 5:56 pmBOS Boston Logan Intl-EYW Key West
8h 28m1 stop Washington, D.C. Reagan-National
$229American Airlines
Wed, Nov 11
9:26 am - 5:15 pmBOS Boston Logan Intl-EYW Key West
7h 49m2 stops Charlotte Douglas Miami
$234American Airlines
Recent last minute American Airlines flight deals to Key West
Tue, Oct 6 - Tue, Oct 13
8:59 am - 4:11 pmCVG Cincinnati Cinci./N. Kentucky-EYW Key West
7h 12m1 stop Charlotte Douglas
10:24 am - 8:35 pmEYW Key West-CVG Cincinnati Cinci./N. Kentucky
10h 11m2 stops Miami Washington, D.C. Reagan-National
$424American Airlines
Tue, Oct 6 - Tue, Oct 13
7:30 am - 1:35 pmEWR Newark-EYW Key West
6h 05m1 stop Charlotte Douglas
8:03 pm - 12:53 amEYW Key West-EWR Newark
4h 50m1 stop Miami
$443American Airlines
Tue, Oct 6 - Tue, Oct 13
8:59 am - 4:11 pmCVG Cincinnati Cinci./N. Kentucky-EYW Key West
7h 12m1 stop Charlotte Douglas
1:43 pm - 11:13 pmEYW Key West-CVG Cincinnati Cinci./N. Kentucky
9h 30m2 stops Miami Chicago O'Hare Intl
$447American Airlines
Tue, Oct 6 - Tue, Oct 13
6:00 am - 12:57 pmCVG Cincinnati Cinci./N. Kentucky-EYW Key West
6h 57m2 stops Washington, D.C. Reagan-National Miami
10:24 am - 8:35 pmEYW Key West-CVG Cincinnati Cinci./N. Kentucky
10h 11m2 stops Miami Washington, D.C. Reagan-National
$451American Airlines
Thu, Oct 8 - Wed, Oct 14
11:57 am - 7:33 pmDCA Washington, D.C. Reagan-National-EYW Key West
7h 36m1 stop Miami
10:24 am - 2:49 pmEYW Key West-DCA Washington, D.C. Reagan-National
4h 25m1 stop Miami
$459American Airlines
Tue, Oct 6 - Tue, Oct 13
6:59 am - 2:19 pmBOS Boston Logan Intl-EYW Key West
7h 20m1 stop Washington, D.C. Reagan-National
8:03 pm - 12:59 amEYW Key West-BOS Boston Logan Intl
4h 56m1 stop Miami
$473American Airlines
Tue, Oct 6 - Tue, Oct 13
6:00 am - 4:11 pmCVG Cincinnati Cinci./N. Kentucky-EYW Key West
10h 11m2 stops Washington, D.C. Reagan-National Charlotte Douglas
1:43 pm - 11:13 pmEYW Key West-CVG Cincinnati Cinci./N. Kentucky
9h 30m2 stops Miami Chicago O'Hare Intl
$474American Airlines
Wed, Oct 7 - Sat, Oct 10
11:05 am - 4:58 pmLGA New York LaGuardia-EYW Key West
5h 53m1 stop Miami
5:28 pm - 11:44 pmEYW Key West-LGA New York LaGuardia
6h 16m1 stop Miami
$477American Airlines
Tue, Oct 6 - Tue, Oct 13
9:26 am - 4:58 pmBOS Boston Logan Intl-EYW Key West
7h 32m2 stops Washington, D.C. Reagan-National Miami
8:03 pm - 12:59 amEYW Key West-BOS Boston Logan Intl
4h 56m1 stop Miami
$478American Airlines
Tue, Oct 6 - Tue, Oct 13
8:59 am - 4:11 pmCVG Cincinnati Cinci./N. Kentucky-EYW Key West
7h 12m1 stop Charlotte Douglas
10:24 am - 7:21 pmEYW Key West-CVG Cincinnati Cinci./N. Kentucky
8h 57m2 stops Miami Chicago O'Hare Intl
$479American Airlines
Recent direct American Airlines flight deals to Key West
Mon, Nov 2 - Wed, Nov 11
12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$292American Airlines
Mon, Nov 2 - Wed, Nov 11
12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$293American Airlines
Sat, Nov 14 - Wed, Nov 18
11:49 am - 4:15 pmORD Chicago O'Hare Intl-EYW Key West
3h 26mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$326American Airlines
Tue, Nov 17 - Sat, Nov 21
3:15 pm - 6:25 pmDCA Washington, D.C. Reagan-National-EYW Key West
3h 10mnonstop
5:28 pm - 8:18 pmEYW Key West-DCA Washington, D.C. Reagan-National
2h 50mnonstop
$339American Airlines
Sat, Nov 14 - Wed, Nov 18
11:49 am - 4:15 pmORD Chicago O'Hare Intl-EYW Key West
3h 26mnonstop
6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$353American Airlines
Sat, Nov 14 - Tue, Nov 17
11:49 am - 4:15 pmORD Chicago O'Hare Intl-EYW Key West
3h 26mnonstop
6:35 pm - 9:30 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$359American Airlines
Sun, Dec 20 - Fri, Dec 25
9:09 am - 1:28 pmBOS Boston Logan Intl-EYW Key West
4h 19mnonstop
1:58 pm - 5:40 pmEYW Key West-BOS Boston Logan Intl
3h 42mnonstop
$367American Airlines
Sat, Dec 5 - Sat, Dec 12
10:00 am - 1:52 pmBOS Boston Logan Intl-EYW Key West
3h 52mnonstop
2:25 pm - 5:58 pmEYW Key West-BOS Boston Logan Intl
3h 33mnonstop
$377American Airlines
Wed, Oct 28 - Sun, Nov 1
10:16 am - 1:30 pmDCA Washington, D.C. Reagan-National-EYW Key West
3h 14mnonstop
7:00 pm - 9:48 pmEYW Key West-DCA Washington, D.C. Reagan-National
2h 48mnonstop
$386American Airlines
Sat, Nov 7 - Thu, Nov 12
11:49 am - 4:15 pmORD Chicago O'Hare Intl-EYW Key West
3h 26mnonstop
5:05 pm - 8:00 pmEYW Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
$386American 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 $381 (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 $527 and $515 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 $194 one-way, and $367 round-trip on the route from Boston to Key West. The most popular route is from Washington, D.C. Reagan-National Airport to Key West and the cheapest ticket found on this route in the last 5 days was $339 return.
How many direct flights does American Airlines operate to Key West every week?
Each week there are around 66 direct flights from within the United States to Key West. The most common day for departures is Friday, 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 $462. On the other hand, the most expensive day to fly is Sunday, where prices are $608 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 $477 on average.
Good to know
Low season | August |
|---|---|
High season | February |
Cheapest flight | $194 |
Average price round-trip | $527 |
Good deal one-way | $338 |
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
Top tips for your flights to Key West with American Airlines
American Airlines customer reviews
7.0
10,000 verified ratings
7.4Boarding
6.4Food
6.8Entertainment
7.2Comfort
7.9Crew
Traveler rating:
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Date
It was OK, but it was delayed about an hour, and my luggage didn't arrive till about an hour and a half after the flight
Terrible. Never flying AA again.
First no airplane at the gate because the previous flight was canceled (and they didn't know?) Then we board and there's a maintenance issue. Then we're told the technician doesnt have the right certification and they need to call another. Then FINALLY we are taxiing. But wait! Flight plans expire after 3 hours and we were not granted permission to take off. So taxi was halted while a new flight plan was filed. Then....no beverage service. Never flying American Airlines again. If they mess up operations this much, how good can their maintenance or training possibly be?
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
Crew did a great job, but aircraft was old and bitterly cold. Arrived early in CLT but had to wait for 30 mins for a gate. I knew in the plane what time we were arriving 8 hours before landing and it's basically an American Airlines airport, think they would have had space for an international flight lined up lol
Plane was late. Rescheduled my appointments
Uncomfortable, not managing boarding process and managing people in the way waiting to board at a later time. Terrible delays
Two hours late, and no communication.
Nothing went well. The crew timed out, they sent us to 7 different gates, my original flight got delayed 8.5 hours, and the best American could do was give us a $12 food credit.
5 hour delay!
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Top American Airlines flights
The most popular destinations for flights with American Airlines according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Cabin class types available on flights to Key West
Cabin classes available on flights to Key West. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Key West
Flights from all regions of United States to Key West. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.