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Key Largo

$158+ Cheap flights from Madison (MSN) to Key Largo, FL

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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MIA
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Key Largo are usually found in August or September, booked 80 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Madison to Key Largo

Keep the following information in mind while searching for Madison to Key Largo flight deals. Data was last updated August 28, 2025.

Round-trip from

$269
(Delta)

One-way from

$158
(Frontier)

Popular in

March

Cheapest in

August

Average price

$333
From Madison Truax Field to Key Largo
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One-way flight from Madison Truax Field to Key Largo
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Highest demand for flights based on searches. 7% potential increase in price ($36 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 Key Largo

Cheapest flights from Madison to Key Largo
Explore the most affordable flight options available from Madison to Key Largo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2025.

This Delta deal was found by Cheapflights users on 8/26. 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 9/276:00 amMSN - MIA
1 stop6h 34mDelta
Sun 10/56:00 amMIA - MSN
1 stop4h 58mDelta
Deal found 8/26$269
This United Airlines deal was found by Cheapflights users on 8/26. 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 11/412:26 pmMSN - MIA
2 stops9h 38mUnited Airlines
Tue 11/114:42 pmMIA - MSN
1 stop7h 03mUnited Airlines
Deal found 8/26$274
This United Airlines deal was found by Cheapflights users on 8/26. 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 9/236:30 amMSN - MIA
2 stops9h 40mUnited Airlines
Tue 9/301:15 pmMIA - MSN
2 stops10h 13mUnited Airlines
Deal found 8/26$279
This American Airlines deal was found by Cheapflights users on 8/28. 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 12/66:40 amMSN - MIA
Nonstop3h 34mAmerican Airlines
Wed 12/102:32 pmMIA - MSN
1 stop8h 24mAmerican Airlines
Deal found 8/28$284
This United Airlines deal was found by Cheapflights users on 8/26. 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 9/68:15 amMSN - MIA
1 stop5h 55mUnited Airlines
Wed 10/14:56 pmMIA - MSN
1 stop6h 37mUnited Airlines
Deal found 8/26$288
This Delta deal was found by Cheapflights users on 8/28. 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 12/67:00 amMSN - MIA
1 stop6h 37mDelta
Tue 12/96:00 amMIA - MSN
1 stop5h 15mDelta
Deal found 8/28$292
This Delta deal was found by Cheapflights users on 8/28. 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 10/307:05 amMSN - MIA
1 stop8h 31mDelta
Sat 11/17:00 amMIA - MSN
1 stop6h 59mDelta
Deal found 8/28$294
This United Airlines deal was found by Cheapflights users on 8/26. 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 9/108:15 amMSN - MIA
1 stop5h 55mUnited Airlines
Wed 10/11:15 pmMIA - MSN
2 stops10h 13mUnited Airlines
Deal found 8/26$299
This Delta deal was found by Cheapflights users on 8/27. 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 11/261:35 pmMSN - MIA
1 stop6h 56mDelta
Tue 12/26:40 pmMIA - MSN
2 stops19h 16mDelta
Deal found 8/27$301
This United Airlines deal was found by Cheapflights users on 8/27. 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 9/248:15 amMSN - MIA
2 stops9h 56mUnited Airlines
Wed 10/11:15 pmMIA - MSN
2 stops10h 18mUnited Airlines
Deal found 8/27$303

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Key Largo 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 August 28, 2025.
Use the filters below to find and compare flights from Madison to Key Largo that are best for you.

Fly from

Madison

Fly to

Key Largo

Route

Depart

Return

Price

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 11/26

1:35 pm-9:31 pm

1 stop6h 56m

Miami

Tue 12/2

1:45 pm-8:12 pm

1 stop7h 27m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 9/27

7:30 am-1:57 pm

1 stop5h 27m

Miami

Tue 10/7

6:50 am-12:15 pm

1 stop6h 25m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 10/28

7:05 am-4:36 pm

1 stop8h 31m

Miami

Wed 11/5

11:50 am-7:06 pm

1 stop8h 16m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 9/19

2:48 pm-10:55 pm

1 stop7h 07m

Miami

Sat 9/27

2:27 pm-9:21 pm

1 stop7h 54m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 9/25

11:16 am-8:38 pm

1 stop8h 22m

Miami

Sun 9/28

5:18 am-10:31 am

1 stop6h 13m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Mon 10/27

5:15 pm-11:09 pm

1 stop4h 54m

Miami

Wed 11/5

12:20 pm-4:36 pm

1 stop5h 16m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 10/25

1:25 pm-8:47 pm

1 stop6h 22m

Miami

Sat 11/1

6:00 am-12:26 pm

1 stop7h 26m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 9/27

7:30 am-4:43 pm

1 stop8h 13m

Miami

Sun 10/5

5:18 am-10:31 am

1 stop6h 13m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 10/29

11:00 am-5:53 pm

1 stop5h 53m

Miami

Tue 11/4

10:40 am-4:21 pm

1 stop6h 41m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 10/30

8:00 pm-6:19 am

1 stop9h 19m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/28

Showing 1-10 of 16 results
1
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Best time to book a flight from Madison to Key Largo

Have a flexible travel schedule? Discover the best time to fly to Key Largo 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 Key Largo

How far ahead should I book a flight from Madison to Key Largo?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Key Largo. Price data was last updated on August 22, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Key Largo, you should look to book at least 80 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Madison to Key Largo?

Currently, September is the cheapest month in which you can book a flight from Madison to Key Largo (average of $232). Flying from Madison to Key Largo in March is currently the most expensive (average of $289). 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.

What is the cheapest time of day to fly from MSN to KE9?

Find hourly flight availability from Madison to Key Largo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Key Largo as you normally would.

Reviews of airlines servicing Key Largo

Get insights into the airlines that provide service to Key Largo. 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 Key Largo. Reviews last updated August 28, 2025.
Read through reviews of airlines operating flights from Madison to Key Largo, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

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
8,944 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

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
7,977 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Overall

8.0

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 Key Largo. 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 Key Largo?

    Most people fly from Madison Truax Field (MSN) if they book a flight from Madison to Key Largo. On average, Truax Field has 0 outbound flights to Key Largo per day from 3 airlines. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • How long is the flight from Madison to Key Largo?

    Departing from Madison to Key Largo will take you 5h 27m. There are 1301 mi between Madison and Key Largo. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Madison to Key Largo?

    The cheapest flight price from Madison to Key Largo is $249. On average you can expect to pay $583. The most popular route, (Madison Truax Field - Miami), can usually be booked for $269.

  • Can I find deals for flights from Madison to Key Largo that include hotel bookings?

    Yes. In addition to deals on Madison to Key Largo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Key Largo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Key Largo.

  • Can I find deals for business class flights from Madison to Key Largo?

    Yes. Cheapflights offers flight deals from Madison to Key Largo 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 Key Largo?

    Currently, September is the cheapest month in which you can book a flight from Madison to Key Largo (average of $232). Flying from Madison to Key Largo in March is currently the most expensive (average of $289). 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 Key Largo

Discover the top 3 airlines that operate flights from Madison to Key Largo. 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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$447FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$440FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$492FlexibilityNo cancel feeOn-time69%

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