$142 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 1/28. 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$259
Key West
Key West1 stop$269
Miami
Miami1 stop$259
Key West
Key West1 stop$269

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

Wed, Jan 28 - Wed, Feb 4
Delta Logo
5:38 am - 1:48 pmMSN-EYW
7h 10m1 stop
Delta Logo
1:28 pm - 7:15 pmEYW-MSN
6h 47m1 stop
$259Delta
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Tue, Jan 13 - Fri, Jan 23
United Airlines Logo
8:15 am - 3:05 pmMSN-MIA
5h 50m1 stop
United Airlines Logo
5:40 pm - 11:44 pmMIA-MSN
7h 04m1 stop
$259United Airlines
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Wed, Jan 28 - Tue, Feb 3
Delta Logo
5:38 am - 1:48 pmMSN-EYW
7h 10m1 stop
Delta Logo
7:10 am - 2:05 pmEYW-MSN
7h 55m2 stops
$264Delta
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Tue, Jan 13 - Fri, Jan 23
United Airlines Logo
6:00 am - 2:38 pmMSN-MIA
7h 38m1 stop
United Airlines Logo
11:00 am - 7:07 pmMIA-MSN
9h 07m2 stops
$264United Airlines
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Wed, Dec 17 - Thu, Dec 25
Delta Logo
11:44 am - 8:06 pmMSN-EYW
7h 22m1 stop
Delta Logo
7:25 am - 12:32 pmEYW-MSN
6h 07m1 stop
$269Delta
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Wed, Mar 25 - Wed, Apr 1
United Airlines Logo
6:30 am - 1:00 pmMSN-MIA
5h 30m1 stop
United Airlines Logo
4:17 pm - 8:54 pmMIA-MSN
5h 37m1 stop
$269United Airlines
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Thu, Jan 29 - Mon, Feb 2
Delta Logo
9:42 am - 7:42 pmMSN-EYW
9h 00m2 stops
Delta Logo
6:08 pm - 10:37 pmEYW-MSN
5h 29m1 stop
$274Delta
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Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:27 am - 3:15 pmMSN-EYW
7h 48m1 stop
American Airlines Logo
3:06 pm - 9:18 pmEYW-MSN
7h 12m1 stop
$276American Airlines
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Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
11:29 am - 9:47 pmMSN-EYW
9h 18m2 stops
American Airlines Logo
6:06 am - 4:00 pmEYW-MSN
10h 54m2 stops
$279American Airlines
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Thu, Nov 13 - Sun, Nov 16
Frontier Logo
8:00 pm - 6:19 amMSN-MIA
9h 19m1 stop
Frontier Logo
6:00 am - 7:15 pmMIA-MSN
14h 15m1 stop
$362Frontier
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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 $411, 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 $526 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 21 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$142
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 26% 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 109% 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 $691.

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 $427 one-way - $409 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 7997 reviews
8.2Boarding
7.3Food
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

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.

6.0 GoodAnonymous, Nov 2025BOS - MCO
Read more Delta reviews

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.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

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.

this crew didn't care much. bumping carts into seats more times than i care to remember

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.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

Short flight but an "eager to help" crew made the journey more enjoyable!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

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

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Everything you need to know for your flight to Florida Keys

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