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Florida Keys

$117+ Cheap flights from Madison (MSN) to Florida Keys

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheap flight deals from Madison to Florida Keys

Keep the following information in mind while searching for Madison to Florida Keys flight deals. Data was last updated October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Frontier)

One-way from

$117
(Frontier)

Popular in

March

Cheapest in

August

Average price

$407
Provider with most accurate pricing for Madison Truax Field-Miami flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Miami flights.
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From Madison Truax Field to Florida Keys
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One-way flight from Madison Truax Field to Florida Keys
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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Madison to Florida Keys

Cheapest flights from Madison to Florida Keys
Explore the most affordable flight options available from Madison to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This Frontier deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:00 pmMSN - MIA
1 stop9h 19mFrontier
Sun 11/25:00 amMIA - MSN
1 stop14h 14mFrontier
Deal found 10/22$194
This Frontier deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:00 pmMSN - MIA
1 stop9h 19mFrontier
Mon 11/176:00 amMIA - MSN
1 stop14h 15mFrontier
Deal found 10/20$238
This Frontier deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:59 pmMSN - MIA
1 stop9h 20mFrontier
Sun 11/25:00 amMIA - MSN
1 stop14h 14mFrontier
Deal found 10/22$251
This Frontier deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:59 pmMSN - MIA
1 stop9h 20mFrontier
Mon 11/176:00 amMIA - MSN
1 stop14h 15mFrontier
Deal found 10/22$258
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:30 pmMSN - EYW
1 stop5h 36mDelta
Tue 12/166:10 pmEYW - MSN
1 stop5h 16mDelta
Deal found 10/23$269
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:00 amMSN - MIA
1 stop7h 37mUnited Airlines
Wed 11/2612:23 pmMIA - MSN
1 stop5h 27mUnited Airlines
Deal found 10/22$269
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amMSN - EYW
1 stop9h 07mAmerican Airlines
Tue 12/167:00 amEYW - MSN
2 stops7h 32mAmerican Airlines
Deal found 10/23$274
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:25 amMSN - MIA
1 stop5h 25mUnited Airlines
Tue 11/1811:00 amMIA - MSN
2 stops10h 35mUnited Airlines
Deal found 10/21$274
This Frontier deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:00 pmMSN - MIA
1 stop9h 19mFrontier
Sun 11/166:00 amMIA - MSN
1 stop14h 15mFrontier
Deal found 10/21$285
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:14 pmMSN - EYW
2 stops7h 34mAmerican Airlines
Sat 12/67:00 amEYW - MSN
2 stops10h 09mAmerican Airlines
Deal found 10/21$286
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:00 amMSN - MIA
1 stop6h 32mDelta
Tue 12/23:50 pmMIA - MSN
1 stop7h 36mDelta
Deal found 10/20$289
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:00 pmMSN - MIA
1 stop9h 19mMultiple Airlines
Mon 11/1710:15 pmMIA - MSN
2 stops35h 53mMultiple Airlines
Deal found 10/20$291

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
Use the filters below to find and compare flights from Madison to Florida Keys that are best for you.

Fly from

Madison

Fly to

Florida Keys

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 11/19

12:20 pm-9:48 pm

1 stop8h 28m

Key West

Mon 11/24

6:33 pm-11:30 pm

1 stop5h 57m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 12/13

1:30 pm-8:06 pm

1 stop5h 36m

Key West

Tue 12/16

6:10 pm-10:26 pm

1 stop5h 16m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 11/19

6:00 am-2:37 pm

1 stop7h 37m

Miami

Wed 11/26

12:23 pm-5:50 pm

1 stop6h 27m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 1/31

6:00 am-4:34 pm

1 stop9h 34m

Miami

Thu 2/5

5:40 pm-11:44 pm

1 stop7h 04m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 1/21

1:16 pm-11:43 pm

1 stop9h 27m

Miami

Tue 1/27

9:45 am-6:44 pm

1 stop9h 59m

$277

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 12/13

10:20 am-9:50 pm

2 stops10h 30m

Key West

Tue 12/16

7:00 am-2:55 pm

2 stops8h 55m

$279

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 12/14

10:55 am-5:34 pm

1 stop5h 39m

Miami

Sat 12/20

6:00 am-10:27 am

1 stop5h 27m

$289

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 11/23

1:30 pm-9:38 pm

1 stop7h 08m

Miami

Thu 11/27

8:05 am-12:45 pm

1 stop5h 40m

$289

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 11/25

6:00 am-1:32 pm

1 stop6h 32m

Miami

Tue 12/2

3:50 pm-10:26 pm

1 stop7h 36m

$289

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 1/18

10:10 am-8:50 pm

1 stop9h 40m

Miami

Sat 1/24

7:30 am-2:39 pm

1 stop8h 09m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 30 results
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2
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Best time to book a flight from Madison to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Florida Keys

What is the cheapest month to book a flight from Madison to Florida Keys?

Currently, November is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $192). Flying from Madison to Florida Keys in June is currently the most expensive (average of $318). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated October 23, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Madison to Florida Keys have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Madison to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Florida Keys?

    Located just 5.4 mi from the city center, Madison Truax Field (MSN) is the airport most travelers will use when flying to Florida Keys from Madison.

  • How long is the flight from Madison to Florida Keys?

    Departing from Madison to Florida Keys will take you 5h 36m. There are 1353 mi between Madison and Florida Keys. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Madison to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Madison to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Florida Keys.

  • Can I find deals for business class flights from Madison to Florida Keys?

    Yes. Cheapflights offers flight deals from Madison to Florida Keys by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Florida Keys?

    Currently, November is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $192). Flying from Madison to Florida Keys in June is currently the most expensive (average of $318). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Madison to Florida Keys

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Top 3 airlines flying from Madison to Florida Keys

Discover the top 3 airlines that operate flights from Madison to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$488FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$348Average$498FlexibilityNo cancel feeOn-time69%

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