HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$108+ Cheap flights from Madison (MSN) to Florida Keys

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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Florida Keys with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Florida Keys

Cheapest flights from Madison to Florida Keys
Explore the most affordable flight options available from Madison to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 5/66:05 pm
MSN
-
MIA
2 stops15h 12m
Multiple Airlines
Sun 5/105:15 am
MIA
-
MSN
1 stop28h 10m
Multiple Airlines
Deal found 2/2$281
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/146:01 am
MSN
-
EYW
1 stop8h 23m
American Airlines
Tue 4/216:49 pm
EYW
-
MSN
1 stop5h 46m
American Airlines
Deal found 2/2$283
This United Airlines deal was found by Cheapflights users on 2/3. 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 4/256:30 am
MSN
-
MIA
1 stop7h 27m
United Airlines
Wed 4/294:13 pm
MIA
-
MSN
1 stop6h 03m
United Airlines
Deal found 2/3$289
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/256:00 am
MSN
-
EYW
2 stops9h 49m
American Airlines
Wed 3/42:26 pm
EYW
-
MSN
1 stop9h 16m
American Airlines
Deal found 2/1$291
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/251:05 pm
MSN
-
EYW
2 stops8h 53m
American Airlines
Wed 4/296:45 am
EYW
-
MSN
2 stops9h 56m
American Airlines
Deal found 2/2$293
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/42:48 pm
MSN
-
EYW
1 stop6h 21m
United Airlines
Wed 3/114:05 pm
EYW
-
MSN
1 stop7h 37m
United Airlines
Deal found 2/2$296
This United Airlines deal was found by Cheapflights users on 2/3. 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 4/146:30 am
MSN
-
MIA
2 stops10h 58m
United Airlines
Tue 4/219:15 am
MIA
-
MSN
2 stops13h 01m
United Airlines
Deal found 2/3$300
This Frontier deal was found by Cheapflights users on 2/3. 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 4/162:33 pm
MSN
-
MIA
1 stop13h 32m
Frontier
Sun 4/195:50 am
MIA
-
MSN
1 stop9h 00m
Frontier
Deal found 2/3$305
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/186:00 am
MSN
-
EYW
1 stop8h 21m
American Airlines
Wed 2/252:26 pm
EYW
-
MSN
1 stop9h 16m
American Airlines
Deal found 2/1$314
This United Airlines deal was found by Cheapflights users on 2/3. 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 4/102:44 pm
MSN
-
MIA
1 stop7h 01m
United Airlines
Sat 4/188:55 am
MIA
-
MSN
1 stop5h 56m
United Airlines
Deal found 2/3$314
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 4/162:44 pm
MSN
-
MIA
1 stop7h 01m
United Airlines
Mon 4/2012:50 pm
MIA
-
MSN
2 stops11h 59m
United Airlines
Deal found 2/2$319
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/316:01 am
MSN
-
MIA
1 stop7h 44m
American Airlines
Tue 4/72:30 pm
MIA
-
MSN
1 stop7h 55m
American Airlines
Deal found 2/3$327

Find flight deals from Madison to Florida Keys

Keep the following information in mind while searching for Madison to Florida Keys flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$283
(American Airlines)

One-way from

$108
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$414
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 Florida Keys
Search Deals
One-way flight from Madison Truax Field to Florida Keys
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($36 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 Florida Keys 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 3, 2026.
Use the filters below to find and compare flights from Madison to Florida Keys that are best for you.

Fly from

Madison

Fly to

Florida Keys

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 3/4

6:30 am-4:07 pm

2 stops8h 37m

Key West

Wed 3/11

4:05 pm-10:42 pm

1 stop7h 37m

$291

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 5/6

6:30 am-6:30 pm

2 stops11h 00m

Miami

Sat 5/9

4:15 pm-9:15 pm

1 stop6h 00m

$294

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 3/3

6:30 am-2:58 pm

1 stop7h 28m

Miami

Tue 3/10

6:00 am-2:58 pm

2 stops9h 58m

$294

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Tue 4/28

6:00 am-2:27 pm

1 stop7h 27m

Miami

Sat 5/2

7:15 am-3:02 pm

2 stops8h 47m

$294

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 4/25

10:05 am-10:28 pm

2 stops11h 23m

Miami

Wed 4/29

4:13 pm-9:16 pm

1 stop6h 03m

$294

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 4/19

2:44 pm-10:45 pm

1 stop7h 01m

Miami

Thu 4/30

4:15 pm-11:59 pm

1 stop8h 44m

$314

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 4/10

2:44 pm-10:45 pm

1 stop7h 01m

Miami

Sat 4/18

8:55 am-1:51 pm

1 stop5h 56m

$314

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 5/20

6:30 am-1:53 pm

1 stop6h 23m

Miami

Mon 5/25

6:30 am-1:53 pm

1 stop8h 23m

$338

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 3/8

7:56 pm-5:38 am

1 stop8h 42m

Miami

Thu 3/12

5:50 am-7:11 pm

1 stop14h 21m

$339

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/14

7:00 am-7:40 pm

2 stops11h 40m

Key West

Tue 4/21

1:22 pm-8:14 pm

1 stop7h 52m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 34 results
1
2
3
4

Best time to book a flight from Madison to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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 Florida Keys

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

Currently, December is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $200). Flying from Madison to Florida Keys in June is currently the most expensive (average of $297). 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated February 3, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Madison to Florida Keys have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

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
8,138 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

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
9,236 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

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
11,216 reviews
Delta
7.9
Good
8,138 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Comfort

7.9

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 Florida Keys. 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 Florida Keys?

    Located just 5.4 mi from the city center, Madison Truax Field (MSN) is the airport most travelers will use when flying to Florida Keys from Madison.

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

    Departing from Madison to Florida Keys will take you 11h. There are 1301 mi between Madison and Florida Keys. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Florida Keys 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 Florida Keys?

    Currently, December is the cheapest month in which you can book a flight from Madison to Florida Keys (average of $200). Flying from Madison to Florida Keys in June is currently the most expensive (average of $297). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
Minneapolis to Orlando flights
O'Hare Intl to Orlando flights
Minneapolis to Fort Myers flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
Minneapolis to Tampa flights
Minneapolis to Miami flights
O'Hare Intl to Fort Myers flights
Minneapolis to Fort Lauderdale flights
Milwaukee to Orlando flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Minneapolis to Sarasota flights
O'Hare Intl to Key West flights
Milwaukee to Tampa flights
Milwaukee to Fort Myers flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Pensacola flights
Minneapolis to Valparaiso flights
Milwaukee to Miami flights
Minneapolis to West Palm Beach flights
Madison to Fort Myers flights
Minneapolis to Pensacola flights
O'Hare Intl to Panama City flights
Appleton to Fort Myers flights
Milwaukee to Fort Lauderdale flights
Appleton to Tampa flights
Appleton to Pensacola flights
Minneapolis to Jacksonville flights
Minneapolis to St Petersburg flights
Madison to Sarasota flights
Green Bay to Pensacola flights
Madison to Tampa flights
Minneapolis to Panama City flights
Madison to Orlando flights
Green Bay to Fort Myers flights
Green Bay to Tampa flights
Appleton to Orlando flights
Madison to Miami flights
Minneapolis to Key West flights
Milwaukee to Sarasota flights
Appleton to Sarasota flights
Appleton to St Petersburg flights
O'Hare Intl to Valparaiso flights
Madison to Fort Lauderdale flights
Appleton to Miami flights
Appleton to Orlando Sanford Intl flights
Milwaukee to Panama City flights
Milwaukee to Pensacola flights

Top 3 airlines flying from Madison to Florida Keys

Discover the top 3 airlines that operate flights from Madison to Florida Keys. 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 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$254Average$392FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$313Average$468FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights