HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$109+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Florida Keys with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$238
(Frontier)

One-way from

$109
(Frontier)

Popular in

March

Cheapest in

June

Average price

$385
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. 12% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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 May 1, 2025.

This Frontier deal was found by Cheapflights users on 4/30. 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 5/157:42 pmMSN - MIA
1 stop8h 40mFrontier
Thu 6/56:00 amMIA - MSN
1 stop13h 58mFrontier
Deal found 4/30$238
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/196:27 amMSN - EYW
1 stop6h 23mAmerican Airlines
Wed 7/234:48 pmEYW - MSN
1 stop8h 02mAmerican Airlines
Deal found 4/30$269
This Delta deal was found by Cheapflights users on 4/30. 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 5/283:45 pmMSN - MIA
1 stop6h 10mDelta
Wed 6/43:19 pmMIA - MSN
1 stop8h 26mDelta
Deal found 4/30$307
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/94:20 pmMSN - MIA
1 stop5h 57mAmerican Airlines
Sun 8/175:55 pmMIA - MSN
1 stop6h 17mAmerican Airlines
Deal found 5/1$334
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 7/196:40 amMSN - MIA
1 stop7h 30mUnited Airlines
Tue 7/291:30 pmMIA - MSN
2 stops10h 03mUnited Airlines
Deal found 4/29$386
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 7/42:54 pmMSN - EYW
2 stops26h 11mUnited Airlines
Tue 7/82:45 pmEYW - MSN
2 stops24h 09mUnited Airlines
Deal found 4/30$419
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/155:30 amMSN - EYW
1 stop6h 26mDelta
Mon 5/196:25 pmEYW - MSN
1 stop5h 36mDelta
Deal found 4/30$529

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 May 1, 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

Thu 5/15

7:42 pm-5:22 am

1 stop8h 40m

Miami

Thu 6/5

6:00 am-6:58 pm

1 stop13h 58m

$238

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 7/19

6:27 am-1:50 pm

1 stop6h 23m

Key West

Wed 7/23

4:48 pm-11:50 pm

1 stop8h 02m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 5/28

3:45 pm-10:55 pm

1 stop6h 10m

Miami

Wed 6/4

3:19 pm-10:45 pm

1 stop8h 26m

$307

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 8/9

4:20 pm-11:17 pm

1 stop5h 57m

Miami

Sun 8/17

5:55 pm-11:12 pm

1 stop6h 17m

$334

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 7/19

6:40 am-3:10 pm

1 stop7h 30m

Miami

Tue 7/29

1:30 pm-10:33 pm

2 stops10h 03m

$386

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/4

2:54 pm-6:05 pm

2 stops26h 11m

Key West

Tue 7/8

2:45 pm-1:54 pm

2 stops24h 09m

$419

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 5/15

7:00 am-8:07 pm

2 stops12h 07m

Key West

Mon 5/19

6:25 pm-11:01 pm

1 stop5h 36m

$458

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 5/15

7:42 pm-5:22 am

1 stop8h 40m

$109

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 7/1

6:10 pm-10:25 am

2 stops15h 15m

$158

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 7/2

6:00 am-8:35 pm

2 stops13h 35m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 results
1
2

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.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Madison to Florida Keys by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

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
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

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
7,934 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

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.
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

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.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $109. Delta flights start at $158 while deals on American Airlines start at $232 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Minneapolis to Miami flights
Minneapolis to Orlando flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to Fort Myers flights
Minneapolis to Tampa flights
O'Hare Intl to Pensacola flights
Minneapolis to Fort Myers flights
O'Hare Intl to Sarasota flights
Milwaukee to Orlando flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Panama City flights
O'Hare Intl to Key West flights
Milwaukee to Miami flights
Appleton to Orlando flights
Milwaukee to Fort Lauderdale flights
Madison to Orlando flights
Minneapolis to Valparaiso flights
Milwaukee to Tampa flights
Milwaukee to Fort Myers flights
O'Hare Intl to Valparaiso flights
Minneapolis to Pensacola flights
Appleton to Tampa flights
Appleton to Fort Myers flights
Minneapolis to West Palm Beach flights
Minneapolis to Jacksonville flights
Milwaukee to Sarasota flights
Appleton to Sarasota flights
Appleton to Fort Lauderdale flights
Madison to Miami flights
Milwaukee to Key West flights
Madison to Panama City flights
Milwaukee to West Palm Beach flights
O'Hare Intl to Daytona Beach flights
Green Bay to Fort Myers flights
Appleton to St Petersburg flights
Milwaukee to Pensacola flights
Madison to West Palm Beach flights
Green Bay to Tampa flights
Milwaukee to Panama City flights
Minneapolis to Key West flights
Appleton to Miami flights
Madison to Sarasota flights
Appleton to Orlando Sanford Intl flights
Appleton to Jacksonville flights
Minneapolis to Panama City flights

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$597FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Privacy Preferences©2025 Cheapflights