$129 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 8/31. 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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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$258
Key West
Key West1 stop$269
Miami
Miami1 stop$258
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

Fri, Aug 29 - Fri, Sep 5
Frontier Logo
7:59 pm - 6:30 amMSN-MIA
9h 31m1 stop
Frontier Logo
6:00 am - 7:14 pmMIA-MSN
14h 14m1 stop
$258Frontier
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Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
6:45 am - 11:07 amMSN-MIA
3h 22mnonstop
American Airlines Logo
7:00 pm - 11:51 pmMIA-MSN
5h 51m1 stop
$259American Airlines
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Fri, Sep 19 - Fri, Sep 26
Frontier Logo
7:59 pm - 12:44 amMSN-MIA
27h 45m1 stop
Frontier Logo
6:00 am - 7:14 pmMIA-MSN
14h 14m1 stop
$267Frontier
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Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
6:45 am - 11:07 amMSN-MIA
3h 22mnonstop
American Airlines Logo
9:35 pm - 11:58 pmMIA-MSN
3h 23mnonstop
$268American Airlines
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Fri, Nov 14 - Tue, Nov 18
American Airlines Logo
6:00 am - 4:16 pmMSN-EYW
9h 16m1 stop
American Airlines Logo
6:33 pm - 11:30 pmEYW-MSN
5h 57m1 stop
$269American Airlines
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Sat, Sep 27 - Tue, Oct 7
American Airlines Logo
5:38 pm - 1:32 amMSN-MIA
6h 54m1 stop
American Airlines Logo
8:40 am - 1:44 pmMIA-MSN
6h 04m1 stop
$269American Airlines
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Thu, Jan 29 - Mon, Feb 2
Delta Logo
12:30 pm - 8:50 pmMSN-MIA
7h 20m1 stop
Delta Logo
8:45 am - 2:39 pmMIA-MSN
6h 54m1 stop
$294Delta
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Sat, Aug 23 - Tue, Aug 26
Delta Logo
1:20 pm - 8:12 pmMSN-EYW
5h 52m1 stop
Delta Logo
6:20 pm - 11:02 pmEYW-MSN
5h 42m1 stop
$304Delta
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Sat, Nov 15 - Sat, Nov 22
United Airlines Logo
6:20 am - 7:08 pmMSN-MIA
11h 48m2 stops
United Airlines Logo
4:11 pm - 8:35 pmMIA-MSN
5h 24m1 stop
$327United Airlines
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Wed, Jan 21 - Tue, Jan 27
United Airlines Logo
7:00 am - 6:35 pmMSN-MIA
10h 35m2 stops
United Airlines Logo
8:00 am - 4:51 pmMIA-MSN
9h 51m2 stops
$359United Airlines
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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 $605, 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 $577 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 6 weeks before departure.


Good to know

Low seasonJune
Cheapest flight$129
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 2% 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 115% 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 $709.

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.
8.0
DeltaOverall score based on 7983 reviews
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
7.9Comfort
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

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.

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.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

The food and sitting need improvements. They were extremely bad.. If you choose to recline, there is no room for the passenger behind you. This is one of the worst sitting arrangements that I ever experience. The aircraft was not properly clean before boarding.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

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.

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

Everything you need to know for your flight to Florida Keys

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