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Madison

$93+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheap 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 agosto 20, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$93
(Frontier)
From Florida Keys to Madison Truax Field
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One-way flight from Florida Keys to Madison Truax Field
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Find 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 agosto 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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.
jue. 10/167:49 pmMIA - MSN
1 stop5h 02mAmerican Airlines
mar. 10/215:46 pmMSN - MIA
1 stop6h 03mAmerican Airlines
Deal found 8/20$269
This American Airlines deal was found by Cheapflights users on 8/20. 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.
vie. 9/194:00 pmMIA - MSN
1 stop7h 57mAmerican Airlines
vie. 9/262:48 pmMSN - MIA
1 stop5h 46mAmerican Airlines
Deal found 8/20$274
This Delta deal was found by Cheapflights users on 8/20. 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.
mié. 10/223:10 pmMIA - MSN
1 stop7h 29mDelta
mar. 10/285:11 pmMSN - MIA
2 stops16h 09mDelta
Deal found 8/20$291
This Delta deal was found by Cheapflights users on 8/20. 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.
mié. 10/223:10 pmMIA - MSN
1 stop7h 29mDelta
lun. 10/275:15 pmMSN - MIA
2 stops16h 05mDelta
Deal found 8/20$307
This Delta deal was found by Cheapflights users on 8/18. 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.
mar. 9/22:38 pmMIA - MSN
1 stop8h 20mDelta
sáb. 9/61:20 pmMSN - MIA
1 stop7h 08mDelta
Deal found 8/18$319
This United Airlines deal was found by Cheapflights users on 8/19. 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.
mié. 9/312:50 pmMIA - MSN
2 stops7h 19mUnited Airlines
dom. 9/78:15 amMSN - MIA
1 stop5h 55mUnited Airlines
Deal found 8/19$324
This American Airlines deal was found by Cheapflights users on 8/18. 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.
jue. 10/96:50 amMIA - MSN
1 stop6h 14mAmerican Airlines
dom. 10/126:00 amMSN - MIA
1 stop7h 22mAmerican Airlines
Deal found 8/18$339
This American Airlines deal was found by Cheapflights users on 8/20. 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.
dom. 10/195:16 amMIA - MSN
1 stop6h 21mAmerican Airlines
dom. 11/25:00 amMSN - MIA
1 stop7h 30mAmerican Airlines
Deal found 8/20$340
This Delta deal was found by Cheapflights users on 8/17. 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.
jue. 8/286:00 amMIA - MSN
1 stop4h 48mDelta
lun. 9/15:40 amMSN - MIA
1 stop6h 53mDelta
Deal found 8/17$349
This United Airlines deal was found by Cheapflights users on 8/20. 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.
mié. 9/1712:50 pmMIA - MSN
2 stops7h 19mUnited Airlines
mié. 9/246:17 amMSN - MIA
1 stop6h 54mUnited Airlines
Deal found 8/20$354
This Delta deal was found by Cheapflights users on 8/18. 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.
jue. 8/2111:52 amEYW - MSN
1 stop5h 20mDelta
lun. 8/255:40 amMSN - EYW
1 stop6h 25mDelta
Deal found 8/18$459
This American Airlines deal was found by Cheapflights users on 8/19. 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.
jue. 8/214:49 pmEYW - MSN
1 stop8h 10mAmerican Airlines
lun. 8/256:06 amMSN - EYW
2 stops9h 40mAmerican Airlines
Deal found 8/19$506

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 agosto 20, 2025.
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

jue. 10/23

8:30 am-12:34 pm

1 stop5h 04m

Madison Truax Field

mar. 10/28

5:11 pm-12:29 am

1 stop6h 18m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

lun. 9/22

12:07 pm-6:45 pm

1 stop7h 38m

Madison Truax Field

mar. 9/30

6:20 am-2:03 pm

1 stop6h 43m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

jue. 10/23

8:30 am-12:34 pm

1 stop5h 04m

Madison Truax Field

lun. 10/27

5:15 pm-11:09 pm

1 stop4h 54m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

mié. 9/17

5:18 am-10:31 am

1 stop6h 13m

Madison Truax Field

mié. 9/24

6:40 am-2:45 pm

1 stop7h 05m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

jue. 10/16

7:49 pm-11:51 pm

1 stop5h 02m

Madison Truax Field

mar. 10/21

5:46 pm-12:49 am

1 stop6h 03m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

mié. 10/22

7:00 am-2:25 pm

1 stop8h 25m

Madison Truax Field

lun. 10/27

5:15 pm-11:09 pm

1 stop4h 54m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

dom. 9/28

5:18 am-10:31 am

1 stop6h 13m

Madison Truax Field

dom. 10/5

7:10 am-1:27 pm

1 stop5h 17m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

mié. 10/22

3:10 pm-9:39 pm

1 stop7h 29m

Madison Truax Field

mar. 10/28

5:11 pm-12:29 am

1 stop6h 18m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

lun. 9/29

12:07 pm-6:45 pm

1 stop7h 38m

Madison Truax Field

sáb. 10/4

6:00 am-2:38 pm

1 stop7h 38m

$269

MiamiMadison

MIA - MSN

MIAMSN

Miami

jue. 10/2

4:00 pm-10:57 pm

1 stop7h 57m

Madison Truax Field

dom. 10/5

6:00 am-2:31 pm

1 stop7h 31m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 22 results
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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 agosto 20, 2025.
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
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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 $269, Delta can have you in Madison from Florida Keys in 5h 04m. Airlines will cover a distance of 1301 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

  • What is the cheapest month to book a flight from Florida Keys to Madison?

    Currently, January is the cheapest month in which you can book a flight from Florida Keys to Madison (average of $338). Flying from Florida Keys to Madison in March is currently the most expensive (average of $422). 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

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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