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Madison

$154+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/156:33 pmEYW - MSN
1 stop6h 07mAmerican Airlines
Tue 1/611:29 amMSN - EYW
2 stops11h 27mAmerican Airlines
Deal found 12/14$384
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/233:30 pmMIA - MSN
1 stop7h 50mAmerican Airlines
Tue 12/3010:00 amMSN - MIA
1 stop8h 27mAmerican Airlines
Deal found 12/16$418
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 12/295:00 amMIA - MSN
1 stop6h 37mAmerican Airlines
Fri 1/23:15 pmMSN - MIA
1 stop7h 36mAmerican Airlines
Deal found 12/16$434
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:16 pmMIA - MSN
Nonstop3h 37mAmerican Airlines
Wed 12/243:15 pmMSN - MIA
1 stop6h 40mAmerican Airlines
Deal found 12/17$505
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/317:15 amMIA - MSN
1 stop5h 33mUnited Airlines
Sun 1/46:00 amMSN - MIA
1 stop7h 31mUnited Airlines
Deal found 12/16$509
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/238:45 amMIA - MSN
2 stops11h 20mUnited Airlines
Tue 12/308:15 amMSN - MIA
1 stop5h 49mUnited Airlines
Deal found 12/17$522
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:15 amMIA - MSN
1 stop5h 33mUnited Airlines
Sun 12/282:29 pmMSN - MIA
1 stop19h 01mUnited Airlines
Deal found 12/17$531
This Delta deal was found by Cheapflights users on 12/16. 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 12/206:00 amMIA - MSN
1 stop5h 27mDelta
Wed 12/245:40 amMSN - MIA
1 stop4h 59mDelta
Deal found 12/16$578
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/164:05 pmEYW - MSN
1 stop5h 42mUnited Airlines
Fri 12/193:46 pmMSN - EYW
1 stop19h 48mUnited Airlines
Deal found 12/15$659
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/154:05 pmEYW - MSN
1 stop5h 42mUnited Airlines
Fri 12/196:40 amMSN - EYW
1 stop28h 54mUnited Airlines
Deal found 12/15$699
This Delta deal was found by Cheapflights users on 12/15. 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 12/167:40 amEYW - MSN
2 stops10h 58mDelta
Fri 12/196:00 amMSN - EYW
2 stops10h 15mDelta
Deal found 12/15$752
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/156:33 pmEYW - MSN
1 stop6h 07mAmerican Airlines
Fri 12/197:00 amMSN - EYW
2 stops9h 09mAmerican Airlines
Deal found 12/15$776

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 December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$301
(Expedia)

One-way from

$154
(Kiwi.com)
Provider with most accurate pricing for Key West-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Key West-Madison Truax Field flights.
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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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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 December 18, 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

Fri 3/6

5:50 am-7:11 pm

1 stop14h 21m

Madison Truax Field

Mon 3/9

7:56 pm-5:38 am

1 stop8h 42m

$301

MiamiMadison

MIA - MSN

MIAMSN

Miami

Sat 2/7

6:37 am-10:55 am

1 stop5h 18m

Madison Truax Field

Sat 2/14

3:20 pm-11:19 pm

1 stop6h 59m

$307

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 3/5

8:05 am-12:43 pm

1 stop5h 38m

Madison Truax Field

Sun 3/8

5:04 pm-12:53 am

1 stop6h 49m

$329

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 2/12

9:50 am-3:30 pm

1 stop6h 40m

Madison Truax Field

Sun 2/15

11:23 am-7:26 pm

1 stop7h 03m

$329

MiamiMadison

MIA - MSN

MIAMSN

Miami

Fri 3/6

6:00 am-10:33 am

1 stop5h 33m

Madison Truax Field

Sun 3/8

5:04 pm-12:53 am

1 stop6h 49m

$329

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 3/5

4:55 pm-11:03 pm

1 stop7h 08m

Madison Truax Field

Mon 3/9

8:09 am-4:20 pm

1 stop7h 11m

$329

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 1/1

6:00 am-10:08 am

1 stop5h 08m

Madison Truax Field

Mon 1/5

7:00 am-1:10 pm

1 stop5h 10m

$353

MiamiMadison

MIA - MSN

MIAMSN

Miami

Wed 1/28

4:54 pm-11:44 pm

1 stop7h 50m

Madison Truax Field

Sat 1/31

6:00 am-4:34 pm

1 stop9h 34m

$387

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 1/21

6:05 pm-2:52 pm

2 stops21h 47m

Madison Truax Field

Sat 1/24

6:30 am-4:22 pm

2 stops8h 52m

$470

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 1/15

8:51 pm-9:08 am

2 stops37h 17m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 27 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 December 18, 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
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Overall

7.9

Entertainment

7.9

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Overall

7.9

Entertainment

7.9

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Overall

7.9

Entertainment

7.9

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 $307, Frontier can have you in Madison from Florida Keys in 5h 18m. 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.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $104. Delta flights start at $145 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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