What airlines fly to Florida Keys?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Florida Keys from Madison according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Florida Keys. Keep in mind that there are 4 different airlines that fly to Florida Keys on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Madison Truax Field to Florida Keys?

Breeze Airways, United Airlines, and Delta are the most popular carriers operating from Madison Truax Field to Florida Keys

When did momondo last update prices for flights from Madison Truax Field Airport to Florida Keys?

Prices for flights from Madison Truax Field Airport to Florida Keys are updated daily.

How many operators does momondo search for flights from Madison Truax Field Airport to Florida Keys?

The number of operators available for flights from Madison Truax Field Airport to Florida Keys is 3 as of August 2026.

How old do you have to be to fly from Madison Truax Field Airport to Florida Keys?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Florida Keys.

What documentation or ID do you need to fly to Florida Keys?

The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$120 Cheap Flights from Madison to Florida Keys in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Florida Keys

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:53 pm - 5:48 amMSN Madison Truax Field-MIA Miami

8h 55m1 stop Denver Intl

7:20 am - 6:58 pmMIA Miami-MSN Madison Truax Field

12h 38m1 stop Denver Intl

$240Frontier

Mon, Nov 9 - Fri, Nov 13

7:55 pm - 4:52 amMSN Madison Truax Field-MIA Miami

7h 57m1 stop Denver Intl

5:50 am - 7:15 pmMIA Miami-MSN Madison Truax Field

14h 25m1 stop Denver Intl

$240Frontier

Sun, Sep 6 - Thu, Sep 10

7:55 pm - 11:25 amMSN Madison Truax Field-EYW Key West

14h 30m1 stop Orlando

12:59 pm - 9:53 amEYW Key West-MSN Madison Truax Field

21h 54m1 stop Tampa

$244Breeze Airways

Sat, Sep 5 - Fri, Sep 11

7:04 am - 4:13 pmMSN Madison Truax Field-EYW Key West

8h 09m1 stop Charlotte Douglas

4:53 pm - 11:49 pmEYW Key West-MSN Madison Truax Field

7h 56m1 stop Charlotte Douglas

$333American Airlines

Thu, Dec 10 - Mon, Dec 14

6:30 am - 12:55 pmMSN Madison Truax Field-EYW Key West

5h 25m1 stop Charlotte Douglas

4:56 pm - 12:10 amEYW Key West-MSN Madison Truax Field

8h 14m1 stop Chicago O'Hare Intl

$333American Airlines

Wed, Aug 26 - Sat, Aug 29

11:19 am - 5:15 pmMSN Madison Truax Field-EYW Key West

4h 56m1 stop Atlanta Hartsfield-Jackson

6:10 pm - 11:03 pmEYW Key West-MSN Madison Truax Field

5h 53m1 stop Atlanta Hartsfield-Jackson

$333Delta

Tue, Oct 20 - Tue, Oct 27

8:10 am - 2:18 pmMSN Madison Truax Field-EYW Key West

5h 08m1 stop Chicago O'Hare Intl

4:00 pm - 9:00 pmEYW Key West-MSN Madison Truax Field

6h 00m1 stop Chicago O'Hare Intl

$333United Airlines

Sat, Sep 26 - Sat, Oct 3

1:28 pm - 9:26 pmMSN Madison Truax Field-MIA Miami

6h 58m1 stop Detroit Metropolitan Wayne County

8:00 am - 12:37 pmMIA Miami-MSN Madison Truax Field

5h 37m1 stop Atlanta Hartsfield-Jackson

$339Delta

Tue, Nov 10 - Sat, Nov 14

3:00 pm - 10:31 pmMSN Madison Truax Field-MIA Miami

6h 31m1 stop Chicago O'Hare Intl

5:28 pm - 11:37 pmMIA Miami-MSN Madison Truax Field

7h 09m1 stop Newark

$339United Airlines

Wed, Oct 28 - Sat, Oct 31

3:00 pm - 10:31 pmMSN Madison Truax Field-MIA Miami

6h 31m1 stop Chicago O'Hare Intl

7:00 am - 11:54 amMIA Miami-MSN Madison Truax Field

5h 54m1 stop Chicago O'Hare Intl

$339United Airlines

Sun, Nov 15 - Sat, Nov 21

Cheap last minute flights

Enter your travel dates to find the best prices.

6:30 am - 12:55 pmMSN Madison Truax Field-EYW Key West

5h 25m1 stop Charlotte Douglas

4:50 pm - 11:09 pmEYW Key West-MSN Madison Truax Field

7h 19m1 stop Charlotte Douglas

$439American Airlines

Wed, Aug 12 - Wed, Aug 19

2:45 pm - 11:11 pmMSN Madison Truax Field-MIA Miami

7h 26m1 stop Chicago O'Hare Intl

6:25 am - 1:15 pmMIA Miami-MSN Madison Truax Field

7h 50m1 stop Charlotte Douglas

$474American Airlines

Fri, Aug 14 - Sun, Aug 23

6:30 am - 12:55 pmMSN Madison Truax Field-EYW Key West

5h 25m1 stop Charlotte Douglas

4:50 pm - 12:10 amEYW Key West-MSN Madison Truax Field

8h 20m2 stops Charlotte Douglas Chicago O'Hare Intl

$508American Airlines

Wed, Aug 12 - Wed, Aug 19

5:00 am - 11:54 amMSN Madison Truax Field-MIA Miami

5h 54m1 stop Chicago O'Hare Intl

3:57 pm - 8:53 pmMIA Miami-MSN Madison Truax Field

5h 56m1 stop Chicago O'Hare Intl

$523United Airlines

Tue, Aug 11 - Sat, Aug 22

6:30 am - 2:54 pmMSN Madison Truax Field-MIA Miami

7h 24m1 stop Chicago O'Hare Intl

12:17 pm - 5:13 pmMIA Miami-MSN Madison Truax Field

5h 56m1 stop Chicago O'Hare Intl

$523United Airlines

Wed, Aug 12 - Wed, Aug 19

5:00 am - 11:54 amMSN Madison Truax Field-MIA Miami

5h 54m1 stop Chicago O'Hare Intl

11:30 am - 8:53 pmMIA Miami-MSN Madison Truax Field

10h 23m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

$528United Airlines

Tue, Aug 11 - Sat, Aug 22

7:55 pm - 5:51 amMSN Madison Truax Field-MIA Miami

8h 56m1 stop Denver Intl

9:33 pm - 8:25 amMIA Miami-MSN Madison Truax Field

35h 52m2 stops San Juan Luis Munoz Marin Intl Raleigh-Durham

$573Multiple Airlines

Tue, Aug 11 - Wed, Aug 12

7:55 pm - 5:51 amMSN Madison Truax Field-MIA Miami

8h 56m1 stop Denver Intl

6:00 am - 7:10 pmMIA Miami-MSN Madison Truax Field

14h 10m1 stop Denver Intl

$763Frontier

Tue, Aug 11 - Sun, Aug 16

7:55 pm - 5:51 amMSN Madison Truax Field-MIA Miami

8h 56m1 stop Denver Intl

6:00 am - 7:10 pmMIA Miami-MSN Madison Truax Field

14h 10m1 stop Denver Intl

$774Frontier

Thu, Aug 13 - Sun, Aug 16

7:00 am - 2:24 pmMSN Madison Truax Field-MIA Miami

6h 24m1 stop New York LaGuardia

7:15 am - 2:27 pmMIA Miami-MSN Madison Truax Field

8h 12m1 stop New York LaGuardia

$941Delta

Tue, Aug 11 - Wed, Aug 12

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

United Airlines flights from Madison to Florida Keys

Our best United Airlines deals on Madison to Florida Keys flight tickets

United Airlines

Oct 31

MSN3:00 pmMadison Truax Field

6h 31m

1 stop

MIA10:31 pmMiami

Nov 7

MIA6:35 amMiami

9h 25m

2 stops

MSN3:00 pmMadison Truax Field

$344

United Airlines

Oct 3

MSN5:00 amMadison Truax Field

8h 51m

2 stops

MIA2:51 pmMiami

Oct 10

MIA1:26 pmMiami

8h 34m

2 stops

MSN9:00 pmMadison Truax Field

$349

United Airlines

Jan 8

MSN8:20 amMadison Truax Field

7h 59m

1 stop

MIA5:19 pmMiami

Jan 16

MIA9:00 amMiami

5h 50m

1 stop

MSN1:50 pmMadison Truax Field

$363

Frontier flights from Madison to Florida Keys

Our best Frontier deals on Madison to Florida Keys flight tickets

Frontier

Sep 6

MSN7:55 pmMadison Truax Field

7h 57m

1 stop

MIA4:52 amMiami

Sep 10

MIA5:50 amMiami

14h 25m

1 stop

MSN7:15 pmMadison Truax Field

$240

Frontier

Sep 13

MSN8:00 pmMadison Truax Field

27h 46m

1 stop

MIA12:46 amMiami

Sep 20

MIA5:50 amMiami

14h 25m

1 stop

MSN7:15 pmMadison Truax Field

$250

Frontier

Aug 20

MSN7:55 pmMadison Truax Field

7h 57m

1 stop

MIA4:52 amMiami

Aug 27

MIA6:00 amMiami

14h 10m

1 stop

MSN7:10 pmMadison Truax Field

$255

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonMiami

MSN Madison Truax Field - MIA Miami

MSNMIA

Madison Truax Field

Mon 11/9

7:53 pm-5:48 am

1 stop8h 55m

Miami

Fri 11/13

7:20 am-6:58 pm

1 stop12h 38m

$240

MadisonMiami

MSN Madison Truax Field - MIA Miami

MSNMIA

Madison Truax Field

Sun 9/6

7:55 pm-4:52 am

1 stop7h 57m

Miami

Thu 9/10

5:50 am-7:15 pm

1 stop14h 25m

$240

MadisonKey West

MSN Madison Truax Field - EYW Key West

MSNEYW

Madison Truax Field

Sat 9/5

7:55 pm-11:25 am

1 stop14h 30m

Key West

Fri 9/11

12:59 pm-9:53 am

1 stop21h 54m

$244

MadisonKey West

MSN Madison Truax Field - EYW Key West

MSNEYW

Madison Truax Field

Thu 12/10

7:04 am-4:13 pm

1 stop8h 09m

Key West

Mon 12/14

4:53 pm-11:49 pm

1 stop7h 56m

$333

MadisonKey West

MSN Madison Truax Field - EYW Key West

MSNEYW

Madison Truax Field

Wed 8/26

6:30 am-12:55 pm

1 stop5h 25m

Key West

Sat 8/29

4:56 pm-12:10 am

1 stop8h 14m

$333

Quickest round-trip

MadisonKey West

MSN Madison Truax Field - EYW Key West

MSNEYW

Madison Truax Field

Tue 10/20

11:19 am-5:15 pm

1 stop4h 56m

Key West

Tue 10/27

6:10 pm-11:03 pm

1 stop5h 53m

$333

MadisonKey West

MSN Madison Truax Field - EYW Key West

MSNEYW

Madison Truax Field

Sat 9/26

8:10 am-2:18 pm

1 stop5h 08m

Key West

Sat 10/3

4:00 pm-9:00 pm

1 stop6h 00m

$333

MadisonMiami

MSN Madison Truax Field - MIA Miami

MSNMIA

Madison Truax Field

Tue 11/10

1:28 pm-9:26 pm

1 stop6h 58m

Miami

Sat 11/14

8:00 am-12:37 pm

1 stop5h 37m

$339

MadisonMiami

MSN Madison Truax Field - MIA Miami

MSNMIA

Madison Truax Field

Wed 10/28

3:00 pm-10:31 pm

1 stop6h 31m

Miami

Sat 10/31

5:28 pm-11:37 pm

1 stop7h 09m

$339

MadisonMiami

MSN Madison Truax Field - MIA Miami

MSNMIA

Madison Truax Field

Sun 11/15

3:00 pm-10:31 pm

1 stop6h 31m

Miami

Sat 11/21

7:00 am-11:54 am

1 stop5h 54m

$339

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Madison to Florida Keys

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Florida Keys?

The month of July is another great option to travel to Florida Keys, with average flight prices from Madison averaging around $371.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Madison to Florida Keys is on a Saturday when prices can be found for as low as $720. The most expensive day to fly to Florida Keys is Monday, with ticket prices averaging around $1,046.

How far in advance should I book a flight from Madison to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $426 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Madison for as low as $319 on momondo.

Can stopping save me money on Madison to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Madison to Florida Keys.

Cheap Madison to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Florida Keys

Fastest flight time	3h 15m
Direct flights	Sun
Airports in Florida Keys	3 airports

The fastest flight from Madison to Florida Keys takes 3h 15m

Direct flights go from Madison to Florida Keys on Sunday. There are no airlines offering direct flights.

There are 3 airports in Florida Keys. From Madison there are direct flights to Miami (MIA).

Search flight deals

Frequently asked questions about flying from Madison to Florida Keys

When did momondo last update prices for flights from Madison Truax Field Airport to Florida Keys?
Prices for flights from Madison Truax Field Airport to Florida Keys are updated daily.
How many operators does momondo search for flights from Madison Truax Field Airport to Florida Keys?
The number of operators available for flights from Madison Truax Field Airport to Florida Keys is 3 as of August 2026.
How old do you have to be to fly from Madison Truax Field Airport to Florida Keys?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Madison to Florida Keys?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Madison to Florida Keys is Embraer 175 (Enhanced Winglets) (16.97% of total bookings). The next most popular plane models are Embraer 175 (10.88%), Boeing 737-900 (10.12%), and Embraer 170 (7.89%).

Best airlines flying from Madison to Florida Keys

Compare and see reviews for airlines that fly from Madison to Florida Keys with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $282	Free Cancellation	Rating 7.1 11,897 reviews	Search American Airlines flights
Delta	PriceFrom $302	Free Cancellation	Rating 7.8 8,497 reviews	Search Delta flights
United Airlines	PriceFrom $313	Free Cancellation	Rating 7.4 10,095 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Florida Keys?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Madison to Florida Keys for you.

Can I find flights from Madison to Florida Keys with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Florida Keys flights to just show those with flexible booking policies.

How can momondo help me find flights from Madison to Florida Keys?

Once you have performed a search for Madison to Florida Keys flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Madison to Florida Keys right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Florida Keys, momondo offers a useful price alert feature which will track prices for flights to Florida Keys from Madison and alert you when they change.