$109 Find Cheap Flights from Madison to Florida Keys

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 3/9. 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 Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Florida Keys, 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 Madison to Florida Keys, as well as popular online travel agencies
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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$334
Key West
Key West1 stop$283
Miami
Miami1 stop$334
Key West
Key West1 stop$283

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

Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
9:56 am - 6:19 pm
MSN
-
EYW
7h 23m
1 stop
American Airlines Logo
6:49 pm - 11:35 pm
EYW
-
MSN
5h 46m
1 stop
$283American Airlines
Tue, Mar 3 - Wed, Mar 11
United Airlines Logo
8:15 am - 3:00 pm
MSN
-
EYW
5h 45m
1 stop
United Airlines Logo
4:05 pm - 10:42 pm
EYW
-
MSN
7h 37m
1 stop
$286United Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
1:05 pm - 10:58 pm
MSN
-
EYW
8h 53m
2 stops
American Airlines Logo
6:49 pm - 11:35 pm
EYW
-
MSN
5h 46m
1 stop
$288American Airlines
Tue, Mar 3 - Wed, Mar 11
United Airlines Logo
6:30 am - 5:54 pm
MSN
-
EYW
10h 24m
2 stops
United Airlines Logo
4:05 pm - 10:42 pm
EYW
-
MSN
7h 37m
1 stop
$291United Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
1:05 pm - 10:58 pm
MSN
-
EYW
8h 53m
2 stops
American Airlines Logo
6:45 am - 3:42 pm
EYW
-
MSN
9h 57m
2 stops
$293American Airlines
Mon, Mar 2 - Wed, Mar 11
American Airlines Logo
6:00 am - 3:57 pm
MSN
-
EYW
8h 57m
2 stops
American Airlines Logo
2:06 pm - 9:39 pm
EYW
-
MSN
8h 33m
2 stops
$297American Airlines
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
2:50 pm - 10:24 pm
MSN
-
MIA
6h 34m
1 stop
United Airlines Logo
9:00 am - 2:57 pm
MIA
-
MSN
6h 57m
1 stop
$334United Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:01 am - 3:24 pm
MSN
-
EYW
8h 23m
1 stop
American Airlines Logo
2:29 pm - 10:27 pm
EYW
-
MSN
8h 58m
1 stop
$336American Airlines
Fri, Apr 10 - Sat, Apr 18
Delta Logo
5:15 pm - 12:52 am
MSN
-
MIA
6h 37m
1 stop
Delta Logo
7:01 am - 1:27 pm
MIA
-
MSN
7h 26m
1 stop
$338Delta
Sun, Mar 8 - Thu, Mar 12
Frontier Logo
7:56 pm - 5:38 am
MSN
-
MIA
8h 42m
1 stop
Frontier Logo
5:50 am - 7:11 pm
MIA
-
MSN
14h 21m
1 stop
$339Frontier
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.

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 $400, 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 August, when tickets cost $326 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $528 and $505 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 5 weeks before departure, which saves you about 2% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$109
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 12% 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.

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

    The cheapest time of day to fly to Florida Keys is generally in the morning, when round-trip flights cost $646 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 $646.

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.
7.9
DeltaOverall score based on 8176 reviews
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

2.0 MediocreAnonymous, Jan 2026
ATL - FLL
Read more Delta reviews

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Plane outlets in my row not working to charge phone. Staff response was, well it should be. Plug into seed for volume not working well. Had to find the sweet spot for plug in or it would shut off and on.

Fine not above and beyond as I had a connection that was delayed due to maintenance

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Flight was on time and the meal and service were good.

Old equipment, needs upgrade and seat comfort. Internet didn't work 75% or the time.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

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

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports