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Key Largo

$89+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MIA
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
1 adult, Economy
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Cheap 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 February 27, 2026.

This American Airlines deal was found by Cheapflights users on 2/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:19 am
MSN
-
MIA
1 stop7h 26m
American Airlines
Sat 4/257:05 am
MIA
-
MSN
1 stop6h 30m
American Airlines
Deal found 2/26$327
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Sun 4/122:44 pm
MSN
-
MIA
1 stop7h 01m
United Airlines
Sat 4/186:15 am
MIA
-
MSN
2 stops9h 55m
United Airlines
Deal found 2/24$333
This American Airlines deal was found by Cheapflights users on 2/23. 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 4/2111:31 am
MSN
-
MIA
1 stop8h 16m
American Airlines
Sat 4/258:30 am
MIA
-
MSN
1 stop7h 01m
American Airlines
Deal found 2/23$334
This Frontier deal was found by Cheapflights users on 2/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:56 pm
MSN
-
MIA
1 stop8h 42m
Frontier
Fri 3/135:50 am
MIA
-
MSN
1 stop14h 21m
Frontier
Deal found 2/26$335
This Frontier deal was found by Cheapflights users on 2/25. 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 5/72:33 pm
MSN
-
MIA
1 stop13h 32m
Frontier
Sun 5/105:50 am
MIA
-
MSN
1 stop9h 00m
Frontier
Deal found 2/25$336
This United Airlines deal was found by Cheapflights users on 2/26. 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 4/142:44 pm
MSN
-
MIA
1 stop7h 01m
United Airlines
Tue 4/219:15 am
MIA
-
MSN
2 stops10h 38m
United Airlines
Deal found 2/26$337
This American Airlines deal was found by Cheapflights users on 2/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/103:29 pm
MSN
-
MIA
1 stop8h 03m
American Airlines
Sat 4/185:05 am
MIA
-
MSN
1 stop7h 00m
American Airlines
Deal found 2/27$338
This Delta deal was found by Cheapflights users on 2/26. 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 3/145:15 pm
MSN
-
MIA
1 stop6h 37m
Delta
Mon 3/167:00 am
MIA
-
MSN
1 stop8h 28m
Delta
Deal found 2/26$339
This United Airlines deal was found by Cheapflights users on 2/26. 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 5/96:30 am
MSN
-
MIA
2 stops10h 48m
United Airlines
Sat 5/167:00 am
MIA
-
MSN
2 stops9h 02m
United Airlines
Deal found 2/26$340
This United Airlines deal was found by Cheapflights users on 2/24. 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 3/1012:13 pm
MSN
-
MIA
2 stops9h 53m
United Airlines
Sat 3/149:00 am
MIA
-
MSN
1 stop6h 57m
United Airlines
Deal found 2/24$344
This Delta deal was found by Cheapflights users on 2/24. 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 5/165:29 pm
MSN
-
MIA
1 stop6h 14m
Delta
Sat 5/236:33 am
MIA
-
MSN
1 stop5h 35m
Delta
Deal found 2/24$347
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/172:44 pm
MSN
-
MIA
1 stop7h 01m
United Airlines
Fri 4/244:13 pm
MIA
-
MSN
1 stop8h 36m
United Airlines
Deal found 2/23$349

Find 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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(American Airlines)

One-way from

$89
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$398
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 Key Largo
Search Deals
One-way flight from Madison Truax Field to Key Largo
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 27, 2026.
Use the filters below to find and compare flights from Madison to Key Largo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 4/14

2:57 pm-10:52 pm

1 stop6h 55m

Miami

Mon 4/20

7:30 am-2:17 pm

1 stop7h 47m

$338

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 5/12

5:29 pm-12:43 am

1 stop6h 14m

Miami

Mon 5/18

6:33 am-11:08 am

1 stop5h 35m

$363

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 4/14

6:30 am-8:58 pm

2 stops13h 28m

Miami

Tue 4/21

9:15 am-9:21 pm

2 stops13h 06m

$379

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 4/28

6:30 am-5:04 pm

2 stops9h 34m

Miami

Sat 5/2

6:15 am-3:02 pm

2 stops9h 47m

$398

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 4/22

8:30 am-6:28 pm

2 stops8h 58m

Miami

Sat 4/25

9:00 am-7:25 pm

2 stops11h 25m

$398

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Mon 4/13

9:00 am-7:54 pm

1 stop9h 54m

Miami

Sat 4/18

9:30 am-9:16 pm

2 stops12h 46m

$418

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 5/15

3:56 pm-10:33 pm

1 stop5h 37m

Miami

Tue 5/19

6:15 am-3:00 pm

2 stops9h 45m

$422

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 3/10

6:30 am-6:31 pm

2 stops11h 01m

Miami

Sat 3/14

9:00 am-2:02 pm

1 stop6h 02m

$424

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 4/19

6:00 am-6:28 pm

2 stops11h 28m

Miami

Fri 4/24

6:00 pm-8:57 am

2 stops15h 57m

$446

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 5/8

2:30 pm-10:33 pm

1 stop7h 03m

Miami

Fri 5/15

4:10 pm-10:39 pm

1 stop7h 29m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 February 20, 2026.

To ensure you get the cheapest price possible for a flight from Madison to Key Largo, you should look to book at least 60 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, April is the cheapest month in which you can book a flight from Madison to Key Largo (average of $66). Flying from Madison to Key Largo in September is currently the most expensive (average of $208). 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 February 27, 2026.

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 February 27, 2026.
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
7.9
Good
8,242 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Boarding

8.1

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
8,242 reviews
Delta
7.9
Good
8,242 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Boarding

8.1

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
9,351 reviews
Delta
7.9
Good
8,242 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Boarding

8.1

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
11,357 reviews
Delta
7.9
Good
8,242 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Boarding

8.1

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 52m. 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 most reliable airlines from Madison to Key Largo?

    Before booking your flight to Key Largo from Madison, check out the most reliable airlines to get you to your destination on time: Qatar Airways (87%), American Airlines (78%), Envoy Air( 78%).

  • 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, April is the cheapest month in which you can book a flight from Madison to Key Largo (average of $66). Flying from Madison to Key Largo in September is currently the most expensive (average of $208). 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 February 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$362FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$250Average$430FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$403FlexibilityNo cancel feeOn-time69%

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