$173 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 7/3. 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

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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Flights Deals

Best Florida Keys Flight Deals from Madison

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$269
Key West
Key West1 stop$269
Miami
Miami1 stop$269
Key West
Key West1 stop$269

Cheap Flights from Madison to Florida Keys

 
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, Nov 19 - Mon, Nov 24
American Airlines Logo
6:38 am - 4:16 pmMSN-EYW
8h 38m1 stop
American Airlines Logo
5:26 pm - 9:24 pmEYW-MSN
4h 58m1 stop
$269American Airlines
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Sat, Jul 12 - Mon, Jul 14
Delta Logo
2:33 pm - 11:07 pmMSN-MIA
7h 34m1 stop
Delta Logo
3:29 pm - 11:05 pmMIA-MSN
8h 36m1 stop
$269Delta
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Wed, Nov 19 - Mon, Nov 24
American Airlines Logo
6:26 am - 6:27 pmMSN-EYW
11h 01m2 stops
American Airlines Logo
5:26 pm - 9:24 pmEYW-MSN
4h 58m1 stop
$274American Airlines
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Mon, Jun 30 - Tue, Jul 8
Delta Logo
5:00 pm - 12:57 amMSN-MIA
6h 57m1 stop
Delta Logo
8:11 am - 12:40 pmMIA-MSN
5h 29m1 stop
$288Delta
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Fri, Sep 5 - Sat, Sep 13
United Airlines Logo
10:50 am - 10:15 pmMSN-MIA
10h 25m2 stops
United Airlines Logo
12:04 pm - 10:23 pmMIA-MSN
11h 19m2 stops
$359United Airlines
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Tue, Jul 1 - Wed, Jul 9
United Airlines Logo
8:10 am - 7:39 pmMSN-MIA
10h 29m2 stops
United Airlines Logo
4:16 pm - 10:33 pmMIA-MSN
7h 17m1 stop
$373United Airlines
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Thu, Sep 4 - Sun, Sep 7
Frontier Logo
8:14 pm - 6:19 amMSN-MIA
9h 05m1 stop
Frontier Logo
6:00 am - 7:29 pmMIA-MSN
14h 29m1 stop
$379Frontier
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Fri, Nov 7 - Sun, Nov 16
Frontier Logo
7:56 pm - 6:19 amMSN-MIA
9h 23m1 stop
Frontier Logo
6:00 am - 6:56 pmMIA-MSN
13h 56m1 stop
$384Frontier
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Wed, Nov 19 - Mon, Nov 24
Breeze Airways Logo
9:48 am - 10:31 amMSN-EYW
47h 43m2 stops
Breeze Airways Logo
11:11 am - 9:08 amEYW-MSN
46h 57m3 stops
$1,113Breeze Airways
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Wed, Nov 19 - Mon, Nov 24
Breeze Airways Logo
9:48 am - 10:31 amMSN-EYW
47h 43m2 stops
Breeze Airways Logo
11:11 am - 9:08 amEYW-MSN
46h 57m3 stops
$1,144Breeze Airways
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Useful Info

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 $603, 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 $330 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $573 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 Wednesday, 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 12 weeks before departure.


Good to know

Low seasonAugust
High seasonJanuary
Cheapest flight$173
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 106% 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 $680.

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 $210 one-way - $742 round-trip

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.
8.0
DeltaOverall score based on 7950 reviews
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

10.0 ExcellentTim, Jun 2025MSP - BUF
Read more Delta reviews

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

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.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Checking in at the counter was very disappointing. The lady had a very bad attitude and smart at me. She had no smile, did not greet me by name, or acknowledge me as a valued customer. Poor reflection of the airline.

Everything you need to know for your flight to Florida Keys

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