$91 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$282
Key West
Key West1 stop$286
Miami
Miami1 stop$282
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

Fri, Mar 6 - Thu, Mar 12
Frontier Logo
7:56 pm - 5:38 am
MSN
-
MIA
8h 42m1 stop
Frontier Logo
5:50 am - 7:11 pm
MIA
-
MSN
14h 21m1 stop
$282Frontier
Fri, Jan 23 - Tue, Jan 27
American Airlines Logo
6:00 am - 4:07 pm
MSN
-
EYW
9h 07m1 stop
American Airlines Logo
6:43 pm - 11:47 pm
EYW
-
MSN
6h 04m1 stop
$286American Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
6:00 am - 5:07 pm
MSN
-
EYW
10h 07m2 stops
American Airlines Logo
2:40 pm - 10:41 pm
EYW
-
MSN
9h 01m1 stop
$288American Airlines
Wed, Jan 7 - Mon, Jan 12
American Airlines Logo
6:00 am - 4:07 pm
MSN
-
EYW
9h 07m1 stop
American Airlines Logo
5:21 pm - 10:40 pm
EYW
-
MSN
6h 19m1 stop
$289American Airlines
Fri, Jan 23 - Tue, Jan 27
Delta Logo
9:50 am - 7:40 pm
MSN
-
EYW
8h 50m2 stops
Delta Logo
1:28 pm - 7:15 pm
EYW
-
MSN
6h 47m1 stop
$291Delta
Wed, Feb 25 - Tue, Mar 3
American Airlines Logo
11:23 am - 10:54 pm
MSN
-
EYW
10h 31m2 stops
American Airlines Logo
6:45 am - 2:19 pm
EYW
-
MSN
8h 34m2 stops
$293American Airlines
Wed, Jan 7 - Mon, Jan 12
American Airlines Logo
7:25 am - 6:01 pm
MSN
-
EYW
9h 36m2 stops
American Airlines Logo
5:21 pm - 10:40 pm
EYW
-
MSN
6h 19m1 stop
$294American Airlines
Fri, Jan 23 - Tue, Jan 27
Delta Logo
9:50 am - 7:40 pm
MSN
-
EYW
8h 50m2 stops
Delta Logo
7:10 am - 3:44 pm
EYW
-
MSN
9h 34m2 stops
$296Delta
Wed, Jan 21 - Tue, Jan 27
United Airlines Logo
10:45 am - 8:29 pm
MSN
-
MIA
8h 44m2 stops
United Airlines Logo
9:00 am - 2:10 pm
MIA
-
MSN
6h 10m1 stop
$312United Airlines
Wed, Feb 4 - Tue, Feb 10
United Airlines Logo
10:45 am - 8:49 pm
MSN
-
MIA
9h 04m2 stops
United Airlines Logo
7:15 am - 2:52 pm
MIA
-
MSN
8h 37m2 stops
$317United 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.

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 $413, 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 March and May, when the average cost of round-trip tickets is $520 and $478 respectively.

What’s the cheapest day of the week to fly from Madison to Florida Keys?

The average price of all round-trip flights from Madison to Florida Keys clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Florida Keys on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Madison to Florida Keys. For your return ticket, we recommend flying on a Friday and avoiding Saturdays for the best deals.

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 seasonSeptember
Cheapest flight$91
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 13% 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 evening, when round-trip flights cost $330 on average. Morning departures are around 97% more expensive than evening flights, 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 $651.

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Madison to the following destinations at these prices or less: Miami $420 one-way - $475 round-trip

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 8010 reviews
7.9Entertainment
7.9Comfort
8.5Crew
8.1Boarding
7.3Food
Airline reviews

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)

6.0 GoodJeff, Dec 2025
JFK - MIA
Read more Delta reviews

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.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

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

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports