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Florida Keys

$118+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/3110:00 amMSN - MIA
1 stop8h 27mAmerican Airlines
Tue 1/63:33 pmMIA - MSN
1 stop8h 26mAmerican Airlines
Deal found 12/16$353
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/245:00 amMSN - EYW
1 stop6h 34mUnited Airlines
Wed 12/314:08 pmEYW - MSN
1 stop5h 55mUnited Airlines
Deal found 12/16$386
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/173:35 pmMSN - EYW
1 stop5h 11mAmerican Airlines
Fri 12/264:40 pmEYW - MSN
1 stop8h 19mAmerican Airlines
Deal found 12/16$399
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/3010:00 amMSN - MIA
1 stop8h 27mAmerican Airlines
Tue 1/64:59 pmMIA - MSN
1 stop7h 00mAmerican Airlines
Deal found 12/16$399
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/313:00 pmMSN - MIA
1 stop13h 00mMultiple Airlines
Tue 1/69:59 pmMIA - MSN
2 stops20h 37mMultiple Airlines
Deal found 12/16$413
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/313:00 pmMSN - MIA
1 stop13h 00mMultiple Airlines
Thu 1/86:00 amMIA - MSN
2 stops32h 48mMultiple Airlines
Deal found 12/16$416
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/315:40 amMSN - MIA
1 stop7h 13mDelta
Wed 1/75:50 amMIA - MSN
1 stop5h 28mDelta
Deal found 12/16$424
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/187:00 amMSN - EYW
1 stop7h 57mAmerican Airlines
Fri 12/261:15 pmEYW - MSN
1 stop7h 25mAmerican Airlines
Deal found 12/16$439
This Priceline deal was found by Cheapflights users on 12/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:34 pmMSN - MIA
1 stop11h 26mFrontier
Mon 1/56:05 amMIA - MSN
1 stop8h 56mFrontier
Deal found 12/16$442
This Frontier deal was found by Cheapflights users on 12/15. 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.
Wed 12/243:00 pmMSN - MIA
1 stop13h 00mFrontier
Mon 1/56:05 amMIA - MSN
1 stop8h 56mFrontier
Deal found 12/15$463
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/197:00 amMSN - EYW
1 stop6h 14mAmerican Airlines
Sun 12/214:40 pmEYW - MSN
1 stop8h 19mAmerican Airlines
Deal found 12/16$469
This Delta deal was found by Cheapflights users on 12/15. 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.
Mon 12/225:01 pmMSN - MIA
1 stop5h 38mDelta
Wed 1/711:33 amMIA - MSN
1 stop8h 42mDelta
Deal found 12/15$474

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$282
(Expedia)

One-way from

$118
(Expedia)

Popular in

March

Cheapest in

August

Average price

$471
Provider with most accurate pricing for Madison Truax Field-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Miami flights.
Search Deals
From Madison Truax Field to Florida Keys
Search Deals
One-way flight from Madison Truax Field to Florida Keys
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Sat 4/25

12:22 pm-6:23 pm

1 stop5h 01m

Key West

Wed 4/29

5:14 pm-10:29 pm

1 stop6h 15m

$283

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 2/25

11:23 am-10:54 pm

2 stops10h 31m

Key West

Wed 3/4

6:20 pm-10:57 pm

1 stop5h 37m

$288

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 1/23

9:50 am-7:40 pm

2 stops8h 50m

Key West

Tue 1/27

1:28 pm-7:15 pm

1 stop6h 47m

$291

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

7:25 am-6:01 pm

2 stops9h 36m

Key West

Wed 2/11

5:21 pm-10:40 pm

1 stop6h 19m

$291

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 2/25

9:43 am-10:23 pm

2 stops11h 40m

Key West

Tue 3/3

1:36 pm-10:57 pm

2 stops10h 21m

$293

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 1/17

11:29 am-11:56 pm

2 stops11h 27m

Key West

Wed 1/21

6:06 am-12:46 pm

2 stops7h 40m

$293

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 1/23

11:29 am-9:47 pm

2 stops9h 18m

Key West

Tue 1/27

1:33 pm-10:40 pm

2 stops10h 07m

$296

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 2/4

10:45 am-5:15 pm

1 stop5h 30m

Miami

Tue 2/10

5:40 pm-11:44 pm

1 stop7h 04m

$307

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 3/11

5:04 pm-12:53 am

1 stop6h 49m

Miami

Sat 3/21

7:00 am-2:28 pm

1 stop8h 28m

$307

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 1/24

6:00 am-2:38 pm

1 stop7h 38m

Miami

Sat 1/31

9:05 am-4:51 pm

2 stops8h 46m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 26 results
1
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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 $225). Flying from Madison to Florida Keys in June is currently the most expensive (average of $314). 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 December 18, 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
8,005 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Food

7.3

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
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Food

7.3

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
9,091 reviews
Delta
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Food

7.3

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.9

Food

7.3

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 01m. There are 1353 mi between Madison and Florida Keys. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Madison to Florida Keys one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $114. Delta flights start at $175 while deals on American Airlines start at $175 one-way.

  • 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 $225). Flying from Madison to Florida Keys in June is currently the most expensive (average of $314). 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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$443FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$437FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$312Average$468FlexibilityNo cancel feeOn-time69%

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