HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$103+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida Keys to Madison 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.

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 October 23, 2025.

This Frontier deal was found by Cheapflights users on 10/21. 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 10/306:00 amMIA - MSN
1 stop14h 15mFrontier
Sun 11/27:59 pmMSN - MIA
1 stop9h 20mFrontier
Deal found 10/21$252
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/143:00 pmEYW - MSN
1 stop9h 06mUnited Airlines
Mon 11/176:00 amMSN - EYW
1 stop7h 04mUnited Airlines
Deal found 10/21$269
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/146:33 pmEYW - MSN
1 stop5h 57mAmerican Airlines
Mon 11/176:00 amMSN - EYW
2 stops10h 01mAmerican Airlines
Deal found 10/21$274
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/2310:10 pmMIA - MSN
1 stop12h 20mAmerican Airlines
Tue 12/308:10 pmMSN - MIA
1 stop12h 05mAmerican Airlines
Deal found 10/23$277
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Sat 12/69:18 pmMIA - MSN
Nonstop3h 38mAmerican Airlines
Sat 12/133:55 pmMSN - MIA
1 stop5h 40mAmerican Airlines
Deal found 10/23$279
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/87:53 pmEYW - MSN
1 stop5h 06mAmerican Airlines
Wed 11/123:37 pmMSN - EYW
1 stop5h 11mAmerican Airlines
Deal found 10/21$294
This Frontier deal was found by Cheapflights users on 10/22. 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.
Sun 10/266:00 amMIA - MSN
1 stop12h 51mFrontier
Thu 10/308:00 pmMSN - MIA
1 stop9h 19mFrontier
Deal found 10/22$295
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/245:00 amMIA - MSN
1 stop6h 37mAmerican Airlines
Thu 1/15:55 pmMSN - MIA
1 stop5h 52mAmerican Airlines
Deal found 10/22$314
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/32:29 pmMIA - MSN
1 stop9h 16mUnited Airlines
Mon 12/86:15 amMSN - MIA
1 stop9h 27mUnited Airlines
Deal found 10/21$349
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/175:07 pmMIA - MSN
1 stop6h 53mAmerican Airlines
Sat 11/224:51 pmMSN - MIA
1 stop6h 55mAmerican Airlines
Deal found 10/21$353
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/37:19 pmMIA - MSN
1 stop5h 21mAmerican Airlines
Sat 12/63:55 pmMSN - MIA
1 stop5h 40mAmerican Airlines
Deal found 10/21$369
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 10/287:00 amMIA - MSN
1 stop8h 25mDelta
Wed 11/55:11 pmMSN - MIA
1 stop6h 18mDelta
Deal found 10/20$370

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$103
(Frontier)
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 October 23, 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

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 11/14

3:00 pm-11:06 pm

1 stop9h 06m

Madison Truax Field

Mon 11/17

6:00 am-2:04 pm

1 stop7h 04m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 11/14

6:33 pm-11:30 pm

1 stop5h 57m

Madison Truax Field

Mon 11/17

6:00 am-5:01 pm

2 stops10h 01m

$274

MiamiMadison

MIA - MSN

MIAMSN

Miami

Fri 12/5

4:55 pm-10:26 pm

1 stop6h 31m

Madison Truax Field

Sun 12/7

5:38 am-2:45 pm

1 stop8h 07m

$289

MiamiMadison

MIA - MSN

MIAMSN

Miami

Sat 2/7

8:45 am-5:11 pm

1 stop9h 26m

Madison Truax Field

Sat 2/14

3:26 pm-12:32 am

1 stop8h 06m

$289

MiamiMadison

MIA - MSN

MIAMSN

Miami

Wed 12/3

7:00 am-10:59 am

1 stop4h 59m

Madison Truax Field

Sun 12/7

1:35 pm-9:50 pm

1 stop7h 15m

$289

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 12/4

7:10 pm-11:49 pm

1 stop5h 39m

Madison Truax Field

Sun 12/7

5:00 am-11:15 am

1 stop5h 15m

$289

Key WestMadison

EYW - MSN

EYWMSN

Key West

Sat 11/8

7:53 pm-11:59 pm

1 stop5h 06m

Madison Truax Field

Wed 11/12

3:37 pm-9:48 pm

1 stop5h 11m

$294

MiamiMadison

MIA - MSN

MIAMSN

Miami

Wed 12/24

10:09 am-5:42 pm

2 stops8h 33m

Madison Truax Field

Thu 1/1

5:55 pm-12:47 am

1 stop5h 52m

$319

MiamiMadison

MIA - MSN

MIAMSN

Miami

Wed 12/3

2:29 pm-10:45 pm

1 stop9h 16m

Madison Truax Field

Mon 12/8

6:15 am-4:42 pm

1 stop9h 27m

$349

MiamiMadison

MIA - MSN

MIAMSN

Miami

Fri 3/13

9:00 am-1:52 pm

1 stop5h 52m

Madison Truax Field

Tue 3/17

2:40 pm-10:39 pm

1 stop6h 59m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 25 results
1
2
3

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 October 23, 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
7,982 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

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
7,982 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

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
11,032 reviews
Delta
7.9
Good
7,982 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

7.9

Entertainment

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 $274, United Airlines can have you in Madison from Florida Keys in 5h 57m. Airlines will cover a distance of 1353 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 Frontier, which is currently one of the cheapest options available, starting at $141. Delta flights start at $145 while deals on Breeze Airways start at $249 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

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 Florida Keys to Madison

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

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.