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Florida Keys

$120+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$120
(Frontier)

Popular in

March

Cheapest in

June

Average price

$413
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. 11% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This American Airlines deal was found by Cheapflights users on 4/3. 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 4/196:37 amMSN - EYW
2 stops11h 09mAmerican Airlines
Fri 4/253:56 pmEYW - MSN
2 stops8h 48mAmerican Airlines
Deal found 4/3$249
This United Airlines deal was found by Cheapflights users on 4/4. 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 4/196:30 amMSN - EYW
1 stop7h 34mUnited Airlines
Wed 4/234:04 pmEYW - MSN
1 stop6h 24mUnited Airlines
Deal found 4/4$264
This Delta deal was found by Cheapflights users on 4/4. 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 4/196:20 amMSN - EYW
2 stops9h 57mDelta
Wed 4/231:35 pmEYW - MSN
1 stop9h 22mDelta
Deal found 4/4$273
This United Airlines deal was found by Cheapflights users on 4/3. 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 5/66:30 amMSN - MIA
1 stop7h 26mUnited Airlines
Tue 5/137:53 amMIA - MSN
1 stop10h 01mUnited Airlines
Deal found 4/3$307
This Delta deal was found by Cheapflights users on 4/4. 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 5/276:00 amMSN - MIA
1 stop6h 43mDelta
Fri 5/303:19 pmMIA - MSN
1 stop8h 26mDelta
Deal found 4/4$314
This FlightHub deal was found by Cheapflights users on 4/4. 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.
Thu 4/101:52 pmMSN - MIA
1 stop14h 03mFrontier
Sat 4/198:42 pmMIA - MSN
1 stop17h 20mFrontier
Deal found 4/4$320
This American Airlines deal was found by Cheapflights users on 4/4. 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 5/221:21 pmMSN - MIA
1 stop6h 44mAmerican Airlines
Sun 5/256:00 amMIA - MSN
1 stop5h 49mAmerican Airlines
Deal found 4/4$361
This Mytrip deal was found by Cheapflights users on 4/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/37:15 pmMSN - MIA
3 stops37h 07mMultiple Airlines
Sun 4/610:17 amMIA - MSN
2 stops23h 42mMultiple Airlines
Deal found 4/2$974

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 April 4, 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 4/19

6:37 am-6:46 pm

2 stops11h 09m

Key West

Fri 4/25

3:56 pm-11:44 pm

2 stops8h 48m

$249

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/19

6:30 am-3:04 pm

1 stop7h 34m

Key West

Wed 4/23

4:04 pm-9:28 pm

1 stop6h 24m

$264

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/19

6:20 am-5:17 pm

2 stops9h 57m

Key West

Wed 4/23

1:35 pm-9:57 pm

1 stop9h 22m

$273

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 5/6

6:30 am-2:56 pm

1 stop7h 26m

Miami

Tue 5/13

7:53 am-4:54 pm

1 stop10h 01m

$307

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 5/27

6:00 am-1:43 pm

1 stop6h 43m

Miami

Fri 5/30

3:19 pm-10:45 pm

1 stop8h 26m

$314

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 5/29

7:48 pm-6:30 am

1 stop9h 42m

Miami

Thu 6/5

6:00 am-6:58 pm

1 stop13h 58m

$330

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 5/22

1:21 pm-9:05 pm

1 stop6h 44m

Miami

Sun 5/25

6:00 am-10:49 am

1 stop5h 49m

$361

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 5/1

7:52 pm-5:22 am

1 stop8h 30m

$120

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 7/1

6:10 pm-10:28 am

2 stops15h 18m

$158

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 5/13

6:30 am-4:16 pm

2 stops8h 46m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 15 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 $328). Flying from Madison to Florida Keys in March is currently the most expensive (average of $493). 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 April 4, 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
7,900 reviews

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
7,900 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
8,618 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
7,900 reviews

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
3,276 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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 $120. Delta flights start at $158 while deals on United Airlines start at $198 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 $493). 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$572FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

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