$121 Find Cheap Flights from Madison to Florida Keys - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Florida Keys departing on 10/14. 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.
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1 adult, Economy, 0 bags

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Cheap Flights from Madison to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$260
Key West
Key West1 stop$286
Miami
Miami1 stop$260
Key West
Key West1 stop$286

Book Cheap Madison to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Florida Keys 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 Madison to Florida Keys

Thu, Aug 27 - Sun, Aug 30
Frontier Logo
7:55 pm - 4:52 am
MSN
-
MIA
7h 57m
1 stop
Frontier Logo
6:00 am - 7:10 pm
MIA
-
MSN
14h 10m
1 stop
$260Frontier
Thu, Aug 20 - Thu, Aug 27
Frontier Logo
7:55 pm - 4:52 am
MSN
-
MIA
7h 57m
1 stop
Frontier Logo
6:00 am - 7:10 pm
MIA
-
MSN
14h 10m
1 stop
$275Frontier
Sun, Nov 1 - Fri, Nov 6
Multiple Airlines Logo
6:00 pm - 8:44 am
MSN
-
EYW
13h 44m
1 stop
Multiple Airlines Logo
12:59 pm - 9:53 am
EYW
-
MSN
21h 54m
1 stop
$286Multiple Airlines
Sat, Oct 24 - Fri, Oct 30
Frontier Logo
7:54 pm - 5:48 am
MSN
-
MIA
8h 54m
1 stop
Frontier Logo
7:20 am - 6:58 pm
MIA
-
MSN
12h 38m
1 stop
$294Frontier
Sat, Oct 31 - Fri, Nov 6
Multiple Airlines Logo
10:33 am - 9:22 am
MSN
-
EYW
21h 49m
1 stop
Multiple Airlines Logo
12:59 pm - 9:53 am
EYW
-
MSN
21h 54m
1 stop
$310Multiple Airlines
Sat, Nov 7 - Wed, Nov 11
United Airlines Logo
6:09 am - 1:59 pm
MSN
-
EYW
6h 50m
1 stop
United Airlines Logo
2:55 pm - 11:37 pm
EYW
-
MSN
9h 42m
1 stop
$318United Airlines
Wed, Oct 28 - Wed, Nov 4
Delta Logo
11:28 am - 7:51 pm
MSN
-
EYW
7h 23m
1 stop
Delta Logo
6:11 pm - 10:53 pm
EYW
-
MSN
5h 42m
1 stop
$323Delta
Wed, Aug 12 - Wed, Aug 19
Delta Logo
11:22 am - 7:57 pm
MSN
-
EYW
7h 35m
1 stop
Delta Logo
11:48 am - 4:28 pm
EYW
-
MSN
5h 40m
1 stop
$326Delta
Tue, Nov 3 - Sat, Nov 7
American Airlines Logo
7:08 am - 4:12 pm
MSN
-
EYW
8h 04m
1 stop
American Airlines Logo
8:06 am - 2:44 pm
EYW
-
MSN
7h 38m
1 stop
$329American Airlines
Sat, Oct 24 - Sun, Nov 1
United Airlines Logo
5:00 am - 11:50 am
MSN
-
MIA
5h 50m
1 stop
United Airlines Logo
9:00 am - 1:50 pm
MIA
-
MSN
5h 50m
1 stop
$329United Airlines
Booking Insights

KAYAK's insights & trends for Madison to Florida Keys flights

Get data-powered insights and trends into flights from Madison to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest time of day to fly to Florida Keys?

The average price for all round-trip flights from Madison to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida Keys is generally in the morning, when round-trip flights cost $688 on average. The most expensive time of day to fly to Florida Keys is generally in the morning, which is peak travel time and where the average cost of a ticket is $688.

Can I save money by flying with a layover from Madison to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $462, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Madison to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Florida Keys, 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 Madison to Florida Keys is July, when tickets cost $374 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $502 and $502 respectively.

How far in advance should I book a flight from Madison to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Florida Keys, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low season

September

Cheapest flight

$121
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Madison to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Madison to Florida Keys?

    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 Madison to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Florida Keys 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 Madison to Florida Keys?

    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 Madison to Florida Keys 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 Madison to Florida Keys?

    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 Madison to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Madison to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Madison to Florida Keys. 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 Madison to Florida Keys? 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.
7.8
DeltaOverall score based on 8477 reviews
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
7.8Comfort
Airline reviews

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

4.0 OkayAlexander, Jul 2026
ATL - TPA
Read more Delta reviews

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

It is usually very pleasant. Good service for the price, international flights are even better

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

Horrible experience, delays after delays. A flight that should arrive 11:50pm just landed past 1 am, and another 30min waiting for the baggage to come out. Very disappointing.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports