Florida Keys

$135+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Jan 26 — Feb 21
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Cheap flight deals from Madison to Florida Keys

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Florida Keys (zzEOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$162
(Mytrip)
From Madison Truax Field to Florida Keys
One-way flight from Madison Truax Field to Florida Keys

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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/16:00 amMSN - EYW
1 stop8h 25mAmerican Airlines
Wed 4/94:54 pmEYW - MSN
1 stop6h 55mAmerican Airlines
Deal found 1/20$209
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 10/315:17 pmMSN - MIA
1 stop6h 43mDelta
Tue 11/410:20 amMIA - MSN
1 stop7h 16mDelta
Deal found 1/20$333
This United Airlines deal was found by Cheapflights users on 1/21. 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 4/88:05 amMSN - MIA
1 stop5h 50mUnited Airlines
Mon 4/147:00 amMIA - MSN
1 stop6h 17mUnited Airlines
Deal found 1/21$350
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/46:01 amMSN - MIA
1 stop7h 48mAmerican Airlines
Sat 3/89:30 pmMIA - MSN
Nonstop3h 44mAmerican Airlines
Deal found 1/20$374
This Delta deal was found by Cheapflights users on 1/20. 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 4/295:45 amMSN - EYW
1 stop7h 04mDelta
Fri 5/21:55 pmEYW - MSN
1 stop9h 37mDelta
Deal found 1/20$388
This Frontier deal was found by Cheapflights users on 1/21. 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 4/247:37 pmMSN - MIA
1 stop8h 44mFrontier
Sun 4/276:00 amMIA - MSN
1 stop13h 47mFrontier
Deal found 1/21$410
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/196:16 pmMSN - MIA
2 stops19h 42mMultiple Airlines
Fri 2/219:48 amMIA - MSN
2 stops24h 20mMultiple Airlines
Deal found 1/21$413
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/83:53 pmMSN - EYW
2 stops26h 02mUnited Airlines
Sat 2/1510:00 amEYW - MSN
2 stops12h 14mUnited Airlines
Deal found 1/20$482

Find flights from Madison to Florida Keys within your budget

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 January 21, 2025.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/1

6:00 am-3:25 pm

1 stop8h 25m

Key West

Wed 4/9

4:54 pm-10:49 pm

1 stop6h 55m

$209

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 4/6

6:10 am-1:43 pm

1 stop6h 33m

Miami

Wed 4/9

6:00 am-10:44 am

1 stop5h 44m

$333

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 4/8

8:05 am-2:55 pm

1 stop5h 50m

Miami

Mon 4/14

7:00 am-12:17 pm

1 stop6h 17m

$350

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 3/4

6:01 am-2:49 pm

1 stop7h 48m

Miami

Sat 3/8

9:30 pm-12:14 am

Nonstop3h 44m

$374

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/29

5:45 am-1:49 pm

1 stop7h 04m

Key West

Fri 5/2

1:55 pm-10:32 pm

1 stop9h 37m

$388

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 4/24

7:37 pm-5:21 am

1 stop8h 44m

Miami

Sun 4/27

6:00 am-6:47 pm

1 stop13h 47m

$410

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 2/19

6:16 pm-2:58 pm

2 stops19h 42m

Miami

Fri 2/21

9:48 am-9:08 am

2 stops24h 20m

$413

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 2/25

6:30 am-3:11 pm

1 stop7h 41m

Key West

Mon 3/3

6:00 pm-8:06 pm

2 stops27h 06m

$479

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 4/24

7:37 pm-5:21 am

1 stop8h 44m

$135

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 2/5

6:16 pm-6:44 pm

2 stops23h 28m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 13 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.

Travel insights for flights from Madison to Florida Keys

Get recent, data-driven insights about flights from Madison to Florida Keys including ideal travel times, pricing trends, and more.

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 $531). 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 January 21, 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.
8.0
Very good
8,521 reviews

Comfort

8.0

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.6

Reviews

1 / 10

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.

8.0
Very good
8,521 reviews
8.0
Very good
8,521 reviews

Comfort

8.0

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.6

Reviews

1 / 10

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.

7.4
Good
8,984 reviews
8.0
Very good
8,521 reviews

Comfort

8.0

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.6

Reviews

1 / 10

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.

7.2
Good
10,000 reviews
8.0
Very good
8,521 reviews

Comfort

8.0

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.6

Reviews

1 / 10

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.

6.1
Okay
3,443 reviews
8.0
Very good
8,521 reviews

Comfort

8.0

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.6

Reviews

1 / 10

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 American Airlines, which is currently one of the cheapest options available, starting at $181. United Airlines flights start at $226 while deals on Delta start at $233 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 $531). 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.

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$591FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$249Average$426FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$319Average$498FlexibilityNo cancel feeOn-time69%
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