$66 Find Cheap Flights from Key West to Maryland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Maryland departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Maryland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Maryland, as well as popular online travel agencies
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Flight Deals

Book Cheap Key West to Maryland Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Maryland 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 flight deals from Key West to Maryland

Fri, Mar 6 - Mon, Mar 9
Spirit Airlines Logo
2:25 pm - 11:50 pm
EYW
-
PHL
9h 25m
1 stop
Spirit Airlines Logo
6:00 am - 1:30 pm
PHL
-
EYW
7h 30m
1 stop
$162Spirit Airlines
Fri, Feb 20 - Mon, Mar 23
Multiple Airlines Logo
1:06 pm - 8:19 pm
EYW
-
BWI
7h 13m
1 stop
Multiple Airlines Logo
3:19 pm - 12:21 pm
BWI
-
EYW
21h 02m
2 stops
$221Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
1:06 pm - 7:36 am
EYW
-
PHL
18h 30m
1 stop
Multiple Airlines Logo
5:28 pm - 12:21 pm
PHL
-
EYW
18h 53m
2 stops
$226Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
United Airlines Logo
6:35 pm - 9:25 pm
EYW
-
IAD
2h 50mnonstop
United Airlines Logo
12:50 pm - 4:07 pm
IAD
-
EYW
3h 17mnonstop
$229United Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
1:06 pm - 7:36 am
EYW
-
PHL
18h 30m
1 stop
Multiple Airlines Logo
5:28 pm - 12:21 pm
PHL
-
EYW
18h 53m
2 stops
$232Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
United Airlines Logo
2:15 pm - 9:03 pm
EYW
-
IAD
6h 48m
1 stop
United Airlines Logo
12:50 pm - 4:07 pm
IAD
-
EYW
3h 17mnonstop
$239United Airlines
Fri, May 1 - Sun, May 3
Delta Logo
6:19 pm - 12:42 am
EYW
-
IAD
6h 23m
1 stop
Delta Logo
6:00 am - 11:25 am
IAD
-
EYW
5h 25m
1 stop
$249Delta
Wed, Jun 24 - Mon, Jun 29
Delta Logo
2:35 pm - 9:19 pm
EYW
-
DCA
6h 44m
1 stop
Delta Logo
1:45 pm - 7:44 pm
DCA
-
EYW
5h 59m
1 stop
$274Delta
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
7:45 pm - 12:36 am
EYW
-
DCA
4h 51m
1 stop
American Airlines Logo
8:20 am - 11:26 am
DCA
-
EYW
3h 06mnonstop
$314American Airlines
Wed, Mar 4 - Sun, Mar 8
American Airlines Logo
6:34 pm - 10:55 pm
EYW
-
BWI
4h 21m
1 stop
American Airlines Logo
5:59 pm - 10:37 pm
BWI
-
EYW
4h 38m
1 stop
$326American Airlines
Booking Insights

KAYAK's insights & trends for Key West to Maryland flights

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

What is the cheapest month to fly from Key West to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Maryland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Key West to Maryland is September, when tickets cost $254 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $625 and $577 respectively.

What’s the cheapest day of the week to fly from Key West to Maryland?

The average price of all round-trip flights from Key West to Maryland clicked on KAYAK for each day over the last 12 months.

When flying from Key West to Maryland, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

Good to know

Low seasonDecember
Cheapest flight$66
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 41% increase in price.
Flight from Key West to Philadelphia

FAQs - booking Maryland flights

  • How does KAYAK find such low prices on flights from Key West to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Maryland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Key West to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Key West to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Maryland?

    The cheapest time of day to fly to Maryland is generally in the evening, when round-trip flights cost $398 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the morning, which is peak travel time and where the average cost of a ticket is $440.

Top tips for finding cheap flights to Maryland

  • Looking for a cheap flight? 25% of our users found tickets from Key West to the following destinations at these prices or less: Washington, D.C. $199 one-way - $296 round-trip; Philadelphia $219 one-way - $390 round-trip

Reviews of the top airlines flying from Key West to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Key West to Maryland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8128 reviews
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

10.0 ExcellentSteven, Jan 2026
FLL - CVG
Read more Delta reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

Everything you need to know for your flight from Key West to Maryland

Information on your arrival and departure airports