MSN

$104 Find Cheap Flights from Florida Keys to Madison - Compare and Save

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 6/30. 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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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

Fri, Aug 21 - Tue, Aug 25
United Airlines Logo
3:57 pm - 8:53 pm
MIA
-
MSN
5h 56m
1 stop
United Airlines Logo
6:30 am - 2:54 pm
MSN
-
MIA
7h 24m
1 stop
$217United Airlines
Tue, Aug 11 - Mon, Sep 21
American Airlines Logo
6:38 pm - 11:09 pm
MIA
-
MSN
5h 31m
1 stop
American Airlines Logo
2:17 pm - 8:39 pm
MSN
-
MIA
5h 22m
1 stop
$221American Airlines
Fri, Aug 21 - Tue, Aug 25
United Airlines Logo
3:57 pm - 8:53 pm
MIA
-
MSN
5h 56m
1 stop
United Airlines Logo
5:00 am - 3:55 pm
MSN
-
MIA
9h 55m
2 stops
$222United Airlines
Sat, Aug 22 - Tue, Aug 25
Delta Logo
6:00 am - 12:22 pm
MIA
-
MSN
7h 22m
1 stop
Delta Logo
9:32 am - 5:37 pm
MSN
-
MIA
7h 05m
1 stop
$248Delta
Fri, Jul 17 - Mon, Jul 20
American Airlines Logo
7:21 pm - 12:10 am
MIA
-
MSN
5h 49m
1 stop
American Airlines Logo
5:00 am - 12:45 pm
MSN
-
MIA
6h 45m
1 stop
$273American Airlines
Mon, Jul 6 - Thu, Jul 9
American Airlines Logo
6:40 am - 12:48 pm
MIA
-
MSN
7h 08m
1 stop
American Airlines Logo
5:00 am - 12:45 pm
MSN
-
MIA
6h 45m
1 stop
$288American Airlines
Sat, Aug 22 - Tue, Aug 25
United Airlines Logo
11:30 am - 8:53 pm
MIA
-
MSN
10h 23m
2 stops
United Airlines Logo
6:30 am - 2:54 pm
MSN
-
MIA
7h 24m
1 stop
$304United Airlines
Sat, Aug 22 - Tue, Aug 25
United Airlines Logo
12:17 pm - 6:56 pm
MIA
-
MSN
7h 39m
1 stop
United Airlines Logo
5:00 am - 3:55 pm
MSN
-
MIA
9h 55m
2 stops
$305United Airlines
Sat, Aug 29 - Wed, Sep 2
United Airlines Logo
3:57 pm - 8:53 pm
MIA
-
MSN
5h 56m
1 stop
United Airlines Logo
7:05 am - 4:31 pm
MSN
-
MIA
8h 26m
1 stop
$307United Airlines
Sun, Jun 28 - Tue, Jun 30
Frontier Logo
6:00 am - 6:59 pm
MIA
-
MSN
13h 59m
1 stop
Frontier Logo
7:59 pm - 5:54 am
MSN
-
MIA
8h 55m
1 stop
$311Frontier
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 6% drop 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 3 airlines serving 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 8405 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Five hour delays every hour, I wish it were all at once

2.0 MediocreAnonymous, Jun 2026
MCO - LGA
Read more Delta reviews

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

The flight had a delay but I made it to my connection. Flight was smooth overall

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

Flights were on time actually early service was good and crew cheerful

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

Flights were on time. Free Wifi on plane. Everything was well organized.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Everything was on time and service on the flight was great!

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

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