MSN

$182 Find Cheap Flights from Florida Keys to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 4/28. 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

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Everything you should know

Cheapest round-trip
$286
American Airlines
Thu 4/16Tue 4/21
EYW - MSN • 1 stop
Cheapest non-stop
$1,010
American Airlines
Sat 2/28Sat 3/7
MIA - MSN • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Florida Keys to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Florida Keys to Madison 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 Florida Keys to Madison

Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
5:42 pm - 11:28 pm
EYW
-
MSN
6h 46m
1 stop
American Airlines Logo
6:10 am - 1:49 pm
MSN
-
EYW
6h 39m
1 stop
$286American Airlines
Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
5:42 pm - 11:28 pm
EYW
-
MSN
6h 46m
1 stop
American Airlines Logo
11:33 am - 10:57 pm
MSN
-
EYW
10h 24m
2 stops
$291American Airlines
Tue, Feb 24 - Wed, May 27
United Airlines Logo
9:00 am - 2:57 pm
MIA
-
MSN
6h 57m
1 stop
United Airlines Logo
6:30 am - 3:09 pm
MSN
-
MIA
7h 39m
1 stop
$302United Airlines
Tue, Feb 24 - Wed, May 27
United Airlines Logo
9:00 am - 2:57 pm
MIA
-
MSN
6h 57m
1 stop
United Airlines Logo
6:30 am - 4:16 pm
MSN
-
MIA
8h 46m
2 stops
$307United Airlines
Fri, Feb 13 - Sun, Feb 22
United Airlines Logo
4:10 pm - 9:07 pm
MIA
-
MSN
5h 57m
1 stop
United Airlines Logo
2:48 pm - 10:29 pm
MSN
-
MIA
6h 41m
1 stop
$314United Airlines
Fri, Feb 13 - Sun, Feb 22
United Airlines Logo
4:10 pm - 9:07 pm
MIA
-
MSN
5h 57m
1 stop
United Airlines Logo
6:30 am - 4:21 pm
MSN
-
MIA
8h 51m
2 stops
$319United Airlines
Tue, Feb 24 - Wed, May 27
United Airlines Logo
8:45 am - 8:48 pm
MIA
-
MSN
13h 03m
2 stops
United Airlines Logo
8:15 am - 10:40 pm
MSN
-
MIA
13h 25m
2 stops
$325United Airlines
Thu, May 14 - Wed, May 20
Delta Logo
7:15 am - 1:52 pm
MIA
-
MSN
7h 37m
1 stop
Delta Logo
6:15 am - 1:30 pm
MSN
-
MIA
6h 15m
1 stop
$338Delta
Fri, Apr 17 - Tue, Apr 21
Delta Logo
7:33 am - 5:49 pm
EYW
-
MSN
11h 16m
2 stops
Delta Logo
10:50 am - 7:40 pm
MSN
-
EYW
7h 50m
2 stops
$352Delta
Fri, Apr 17 - Wed, Apr 22
Breeze Airways Logo
9:49 am - 9:08 am
EYW
-
MSN
24h 19m
1 stop
Breeze Airways Logo
6:36 pm - 9:06 am
MSN
-
EYW
13h 30m
1 stop
$391Breeze Airways
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$182
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Miami to Madison

FAQs for booking flights from Florida Keys to Madison

  • How does KAYAK find such low prices on flights from Florida Keys to Madison?

    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 Florida Keys to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida Keys to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from 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 Florida Keys to Madison?

    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 to Madison with an airline and back to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys to Madison?

    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 to Madison from Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Florida Keys to Madison

 
Need help choosing which airline to fly with from Florida Keys to Madison? 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 8130 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

10.0 ExcellentSteven, Jan 2026
FLL - CVG
Read more Delta reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

We were upgraded to First Class and it was a great flight

Little warm on the plane and delayed for an hour

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

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

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