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Florida Keys

$87+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
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 agosto 20, 2025.

Round-trip from

$224
(Expedia)

One-way from

$87
(Frontier)

Popular in

March

Cheapest in

August

Average price

$390
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. 6% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 20, 2025.

This Expedia deal was found by Cheapflights users on 8/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/98:00 pmMSN - MIA
1 stop9h 19mFrontier
vie. 11/146:00 amMIA - MSN
1 stop14h 15mFrontier
Deal found 8/18$224
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/68:00 pmMSN - MIA
1 stop9h 19mFrontier
lun. 11/106:00 amMIA - MSN
1 stop14h 15mFrontier
Deal found 8/18$231
This Frontier deal was found by Cheapflights users on 8/18. 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.
vie. 9/57:59 pmMSN - MIA
2 stops14h 24mFrontier
jue. 9/116:00 amMIA - MSN
1 stop14h 14mFrontier
Deal found 8/18$239
This American Airlines deal was found by Cheapflights users on 8/19. 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.
vie. 9/125:38 pmMSN - MIA
1 stop6h 54mAmerican Airlines
sáb. 9/135:18 amMIA - MSN
1 stop6h 13mAmerican Airlines
Deal found 8/19$263
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/187:59 pmMSN - MIA
1 stop27h 45mFrontier
lun. 9/226:00 amMIA - MSN
1 stop14h 14mFrontier
Deal found 8/18$265
This American Airlines deal was found by Cheapflights users on 8/19. 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.
mié. 9/248:10 amMSN - MIA
1 stop7h 10mAmerican Airlines
dom. 9/285:18 amMIA - MSN
1 stop6h 13mAmerican Airlines
Deal found 8/19$268
This American Airlines deal was found by Cheapflights users on 8/18. 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.
sáb. 12/136:38 amMSN - EYW
1 stop8h 32mAmerican Airlines
mar. 12/163:52 pmEYW - MSN
1 stop8h 02mAmerican Airlines
Deal found 8/18$269
This Delta deal was found by Cheapflights users on 8/18. 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.
sáb. 9/276:00 amMSN - MIA
1 stop6h 34mDelta
dom. 10/56:00 amMIA - MSN
1 stop4h 58mDelta
Deal found 8/18$269
This Frontier deal was found by Cheapflights users on 8/18. 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.
jue. 9/47:59 pmMSN - MIA
2 stops13h 41mFrontier
lun. 9/226:00 amMIA - MSN
1 stop14h 14mFrontier
Deal found 8/18$270
This United Airlines deal was found by Cheapflights users on 8/19. 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.
vie. 9/126:17 amMSN - MIA
1 stop6h 54mUnited Airlines
sáb. 9/1312:04 pmMIA - MSN
2 stops11h 19mUnited Airlines
Deal found 8/19$274
This Frontier deal was found by Cheapflights users on 8/17. 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.
vie. 11/78:00 pmMSN - MIA
2 stops15h 48mFrontier
dom. 11/1610:32 pmMIA - MSN
2 stops21h 43mFrontier
Deal found 8/17$275
This Delta deal was found by Cheapflights users on 8/19. 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.
mar. 12/29:25 amMSN - EYW
2 stops9h 19mDelta
mar. 12/97:00 amEYW - MSN
2 stops10h 36mDelta
Deal found 8/19$304

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 agosto 20, 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

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

dom. 11/9

8:00 pm-6:19 am

1 stop9h 19m

Miami

vie. 11/14

6:00 am-7:15 pm

1 stop14h 15m

$224

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

jue. 11/6

8:00 pm-6:19 am

1 stop9h 19m

Miami

lun. 11/10

6:00 am-7:15 pm

1 stop14h 15m

$231

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

vie. 9/5

7:59 pm-11:23 am

2 stops14h 24m

Miami

jue. 9/11

6:00 am-7:14 pm

1 stop14h 14m

$239

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

jue. 11/6

8:00 pm-6:19 am

1 stop9h 19m

Miami

dom. 11/9

6:00 am-7:15 pm

1 stop14h 15m

$258

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

vie. 11/14

8:00 pm-6:19 am

1 stop9h 19m

Miami

dom. 11/16

6:00 am-7:15 pm

1 stop14h 15m

$258

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

vie. 11/7

8:00 pm-6:19 am

1 stop9h 19m

Miami

dom. 11/9

6:00 am-7:15 pm

1 stop14h 15m

$258

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

vie. 9/12

5:38 pm-1:32 am

1 stop6h 54m

Miami

sáb. 9/13

5:18 am-10:31 am

1 stop6h 13m

$263

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

jue. 9/18

7:59 pm-12:44 am

1 stop27h 45m

Miami

lun. 9/22

6:00 am-7:14 pm

1 stop14h 14m

$265

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

mié. 9/24

8:10 am-4:20 pm

1 stop7h 10m

Miami

dom. 9/28

5:18 am-10:31 am

1 stop6h 13m

$268

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

lun. 1/26

7:00 am-2:48 pm

1 stop6h 48m

Miami

mié. 2/11

11:40 am-8:15 pm

1 stop9h 35m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 27 results
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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, August is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $328). Flying from Madison to Florida Keys in March is currently the most expensive (average of $492). 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 agosto 20, 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
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

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
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

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
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

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
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

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 16m. 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, August is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $328). Flying from Madison to Florida Keys in March is currently the most expensive (average of $492). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$598FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

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