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Madison

$89+ Cheap flights from Florida Keys to Madison (MSN)

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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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Cheap flight deals from Florida Keys to Madison

Cheapest flights from Florida Keys to Madison
Explore the most affordable flight options available from Florida Keys to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:15 am
MIA
-
MSN
1 stop28h 10m
Multiple Airlines
Mon 5/116:50 pm
MSN
-
MIA
2 stops16h 48m
Multiple Airlines
Deal found 2/7$208
This American Airlines deal was found by Cheapflights users on 2/5. 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 4/231:57 pm
EYW
-
MSN
1 stop8h 28m
American Airlines
Tue 4/286:20 am
MSN
-
EYW
1 stop6h 29m
American Airlines
Deal found 2/5$286
This American Airlines deal was found by Cheapflights users on 2/5. 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 3/75:00 am
MIA
-
MSN
1 stop6h 36m
American Airlines
Tue 3/107:15 am
MSN
-
MIA
1 stop6h 11m
American Airlines
Deal found 2/5$327
This Orbitz deal was found by Cheapflights users on 2/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:50 am
MIA
-
MSN
1 stop14h 16m
Frontier
Mon 3/167:51 pm
MSN
-
MIA
1 stop8h 47m
Frontier
Deal found 2/7$339
This American Airlines deal was found by Cheapflights users on 2/5. 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 4/235:42 pm
EYW
-
MSN
1 stop6h 46m
American Airlines
Wed 4/299:18 am
MSN
-
EYW
1 stop7h 58m
American Airlines
Deal found 2/5$339
This United Airlines deal was found by Cheapflights users on 2/5. 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 2/204:10 pm
MIA
-
MSN
1 stop5h 57m
United Airlines
Tue 2/248:15 am
MSN
-
MIA
2 stops9h 01m
United Airlines
Deal found 2/5$344
This United Airlines deal was found by Cheapflights users on 2/5. 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 4/223:47 pm
EYW
-
MSN
1 stop6h 29m
United Airlines
Tue 4/288:30 am
MSN
-
EYW
1 stop5h 21m
United Airlines
Deal found 2/5$363
This United Airlines deal was found by Cheapflights users on 2/6. 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 8/214:05 pm
EYW
-
MSN
1 stop5h 49m
United Airlines
Tue 8/256:45 am
MSN
-
EYW
1 stop7h 21m
United Airlines
Deal found 2/6$366
This United Airlines deal was found by Cheapflights users on 2/5. 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 4/243:47 pm
EYW
-
MSN
1 stop6h 29m
United Airlines
Mon 4/276:30 am
MSN
-
EYW
1 stop7h 21m
United Airlines
Deal found 2/5$369
This United Airlines deal was found by Cheapflights users on 2/5. 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 4/223:47 pm
EYW
-
MSN
1 stop6h 29m
United Airlines
Mon 4/276:30 am
MSN
-
EYW
2 stops9h 12m
United Airlines
Deal found 2/5$371
This Delta deal was found by Cheapflights users on 2/5. 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 4/231:22 pm
EYW
-
MSN
1 stop7h 52m
Delta
Mon 4/275:30 am
MSN
-
EYW
1 stop7h 14m
Delta
Deal found 2/5$379
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:49 am
EYW
-
MSN
1 stop24h 19m
Multiple Airlines
Wed 4/296:36 pm
MSN
-
EYW
2 stops15h 41m
Multiple Airlines
Deal found 2/5$381

Find flight deals from Florida Keys to Madison

Keep the following information in mind while searching for Florida Keys to Madison flight deals. Data was last updated February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Kiwi.com)

One-way from

$89
(Kiwi.com)
Provider with most accurate pricing for Key West-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Madison Truax Field flights.
Search Deals
From Florida Keys to Madison Truax Field
Search Deals
One-way flight from Florida Keys to Madison Truax Field
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to Madison 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 8, 2026.
Use the filters below to find and compare flights from Florida Keys to Madison that are best for you.

Fly from

Florida Keys

Fly to

Madison

Route

Depart

Return

Price

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 5/7

5:15 am-8:25 am

1 stop28h 10m

Madison Truax Field

Mon 5/11

6:50 pm-12:38 pm

2 stops16h 48m

$208

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 4/23

1:57 pm-9:25 pm

1 stop8h 28m

Madison Truax Field

Tue 4/28

6:20 am-1:49 pm

1 stop6h 29m

$286

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 4/23

5:42 pm-11:28 pm

1 stop6h 46m

Madison Truax Field

Wed 4/29

11:35 am-10:58 pm

2 stops10h 23m

$291

MiamiMadison

MIA - MSN

MIAMSN

Miami

Sat 3/7

5:00 am-10:36 am

1 stop6h 36m

Madison Truax Field

Tue 3/10

7:15 am-2:26 pm

1 stop6h 11m

$327

MiamiMadison

MIA - MSN

MIAMSN

Miami

Fri 7/17

8:05 am-12:54 pm

1 stop5h 49m

Madison Truax Field

Tue 7/21

5:17 pm-12:56 am

1 stop6h 39m

$338

MiamiMadison

MIA - MSN

MIAMSN

Miami

Mon 3/9

5:50 am-7:06 pm

1 stop14h 16m

Madison Truax Field

Mon 3/16

7:51 pm-5:38 am

1 stop8h 47m

$339

MiamiMadison

MIA - MSN

MIAMSN

Miami

Fri 2/20

4:10 pm-9:07 pm

1 stop5h 57m

Madison Truax Field

Tue 2/24

8:15 am-6:16 pm

2 stops9h 01m

$344

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 4/22

3:47 pm-9:16 pm

1 stop6h 29m

Madison Truax Field

Tue 4/28

8:30 am-2:51 pm

1 stop5h 21m

$363

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 4/24

3:47 pm-9:16 pm

1 stop6h 29m

Madison Truax Field

Tue 4/28

6:30 am-2:51 pm

1 stop7h 21m

$366

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 4/22

3:47 pm-9:16 pm

1 stop6h 29m

Madison Truax Field

Mon 4/27

6:30 am-2:51 pm

1 stop7h 21m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 28 results
1
2
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Best time to book a flight from Florida Keys to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Florida Keys 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 Florida Keys to Madison
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated February 8, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Florida Keys to Madison to help guide your decision. 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
7.9
Good
8,172 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,172 reviews
Delta
7.9
Good
8,172 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,249 reviews
Delta
7.9
Good
8,172 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Madison. 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 into for flights to Madison from Florida Keys?

    For a flight from Florida Keys to Madison, you will be flying into Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city.

  • How long is the flight from Florida Keys to Madison?

    For as low as $286, American Airlines can have you in Madison from Florida Keys in 8h 28m. Airlines will cover a distance of 1353 mi.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $108. American Airlines flights start at $188 while deals on United Airlines start at $239 one-way.

  • Can I find deals for flights from Florida Keys to Madison that include hotel bookings?

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

  • How can I find direct flights from Florida Keys to Madison?

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

  • Can I find deals for business class flights from Florida Keys to Madison?

    Yes. Cheapflights offers flight deals from Florida Keys to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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