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Find cheap flights from Florida Keys to Madison from $103

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 5/31. 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
0 bags
Mo 6/3
Mo 6/10

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Good to know

Low season

January

High season

July

Cheapest flight

$103
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Key West 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.

See more FAQs

Prefer to fly non-stop from Florida Keys to Madison?

Find which airlines fly direct from Florida Keys to Truax Field, which days they fly and book direct flights.

Nonstop departures

Florida Keys to Madison Truax Field

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights

Nonstop returns

Madison Truax Field to Florida Keys

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights
See more direct flights

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.
8.0
DeltaOverall score based on 10838 reviews
7.4Food
7.9Comfort
8.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

8.0 ExcellentAnonymous, May 2024ATL - ATW
Read more about Delta reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

That flight was smooth, and staff we courteous. it was a full flight so very tight. The boarding through security was not properly controlled. it was rushed and the scanning process for our bags, etc. was pilling up at the other end with no time to empty our belonging my personal items almost toppled over on the floor if i hadn't caught it rapidly. Was it just that time, or always like this - cant say. other than that all else was fine.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

It was terrible because the flight was delayed for 3 hours.

Crowded flight, but upbeat and kind crew. Pilot greeted us at door, flight attendant thanked a number of “special” passengers for their business, another addressed an eight-year old boy as “young man.” United obviously trying to up their game, but though all of that is nice and notable, flying still feels like moving along a human assembly line, being herded into one small space after another (boarding areas with too few seats, planes with limited personal space, shuttles (IAD) packed too full.

Did not like the seat spacing. The seat was very narrow and tight.

United domestic flight was better than international flight. There was no switch to control Ac In international united flight. Food was also average, Air canada food was much better than united.

The flight was clean and on time, the crew were all very nice and we got the seats we booked. Plenty of food and beverages. The seats are too close so it’s very difficult to try and sleep comfortably.

Any flight that gets from point A to B with no drama is excellent.

They cancelled our flight at the last minute due to mechanical issues. Rather, they “delayed” it till the next morning. A pain in the neck when traveling with two young children. Crew was really nice, which made up for it somewhat. This is the second flight from delta that was cancelled this year. Definitely going to fly another airline when possible

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Horrible people at the gate, they force me to check in my carry on, even thought no one behind me has to do it. I had to get out of the airport in NY to get my bag and go thru security again on my way to Honk Kong. The worst part is the employee threatened me with loosing the flights if don’t comply.

Delayed flight, few announcements with information, no comps, cluster f boarding because zones weren’t spread out and announced loud and repeatedly, staff did their job -nothing more nothing less, annoying kids were speaking and kicking the heck out of the back of my seat and parents weren’t willing to parent… so another typical day of air travel in the US.,

Flight was delayed until Next day as crew timed out

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

I was able to get on standby with relative ease

6 plus hour delay with no explanation. No wheelchairs to transport us on arrival. Very disappointed.

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

Book cheap flights from Florida Keys to Madison

Recent round-trip flight deals

5/16Do
1 stopFrontier
7h 44mMIA-MSN
5/18Sa
1 stopFrontier
7h 44mMSN-MIA
$214
5/31Fr
1 stopFrontier
25h 04mMIA-MSN
6/7Fr
1 stopFrontier
7h 48mMSN-MIA
$220
8/13Di
1 stopAmerican Airlines
7h 47mMIA-MSN
8/16Fr
1 stopAmerican Airlines
5h 33mMSN-MIA
$222
5/16Do
1 stopFrontier
7h 44mMIA-MSN
5/18Sa
1 stopFrontier
7h 44mMSN-MIA
$238
6/2So
1 stopFrontier
13h 54mMIA-MSN
6/7Fr
1 stopFrontier
7h 48mMSN-MIA
$287
5/24Fr
1 stopAmerican Airlines
7h 32mMIA-MSN
5/27Mo
1 stopAmerican Airlines
7h 12mMSN-MIA
$290
6/11Di
1 stopDelta
5h 21mMIA-MSN
6/13Do
1 stopDelta
9h 48mMSN-MIA
$292
5/14Di
1 stopDelta
5h 03mMIA-MSN
5/16Do
1 stopDelta
7h 40mMSN-MIA
$309
6/11Di
2 stopsUnited Airlines
22h 57mMIA-MSN
6/13Do
1 stopUnited Airlines
7h 38mMSN-MIA
$510
8/13Di
1 stopUnited Airlines
7h 21mMIA-MSN
8/16Fr
2 stopsUnited Airlines
19h 40mMSN-MIA
$540

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Recent one-way flight deals

5/31Fr
1 stopAmerican Airlines
5h 13mEYW-MSN
$103
6/4Di
1 stopDelta
5h 53mEYW-MSN
$108
5/11Sa
1 stopFrontier
18h 34mMIA-MSN
$109
5/8Mi
1 stopDelta
5h 09mMIA-MSN
$117
7/7So
1 stopFrontier
24h 51mMIA-MSN
$143
5/6Mo
1 stopAmerican Airlines
8h 20mMIA-MSN
$244
5/9Do
1 stopAmerican Airlines
5h 00mMIA-MSN
$248
6/4Di
2 stopsDelta
10h 21mEYW-MSN
$264
6/24Mo
2 stopsUnited Airlines
21h 55mMIA-MSN
$419
6/4Di
3 stopsUnited Airlines
26h 33mEYW-MSN
$431

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Last minute flights from Florida Keys to Madison

Last minute flight, train and bus deals

5/6Mo
multi-stopAmerican Airlines
5h 00mMIA-MSN
5/8Mi
multi-stopAmerican Airlines
7h 24mMSN-MIA
$307
5/9Do
multi-stopFrontier
22h 56mMIA-MSN
5/16Do
multi-stopFrontier
26h 06mMSN-MIA
$333
5/9Do
multi-stopAmerican Airlines
5h 10mMIA-MSN
5/16Do
multi-stopAmerican Airlines
7h 37mMSN-MIA
$678
5/6Mo
multi-stopAmerican Airlines
8h 35mMIA-MSN
5/8Mi
multi-stopAmerican Airlines
5h 01mMSN-MIA
$680
5/9Do
multi-stopAmerican Airlines
9h 59mMIA-MSN
5/16Do
multi-stopAmerican Airlines
7h 37mMSN-MIA
$683
5/6Mo
multi-stopAmerican Airlines
8h 35mMIA-MSN
5/8Mi
multi-stopAmerican Airlines
9h 36mMSN-MIA
$685

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Flights to Madison

Destination:

Madison (MSN)United States

Return flight deals:

Madison - Florida Keys

Cabin classes:

$528
$456
$418
$93

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