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Cheap flights from Madison to Florida Keys from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Florida Keys departing on 8/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Madison to Florida Keys

Cheap round-trip flights

American Airlines Logo
6:45 am - 11:07 amMSN-MIA
3h 22mnonstop
American Airlines Logo
9:35 pm - 11:58 pmMIA-MSN
3h 23mnonstop
$249American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
7:59 pm - 6:30 amMSN-MIA
9h 31m1 stop
Frontier Logo
6:00 am - 7:14 pmMIA-MSN
14h 14m1 stop
$258Frontier
Find Deal
Thu, Aug 28 - Thu, Sep 4
American Airlines Logo
10:21 am - 6:53 pmMSN-MIA
7h 32m1 stop
American Airlines Logo
9:35 pm - 11:58 pmMIA-MSN
3h 23mnonstop
$259American Airlines
Find Deal
Wed, Nov 5 - Sat, Nov 8
Frontier Logo
7:59 pm - 12:44 amMSN-MIA
27h 45m1 stop
Frontier Logo
6:00 am - 7:14 pmMIA-MSN
14h 14m1 stop
$267Frontier
Find Deal
Fri, Sep 19 - Fri, Sep 26
American Airlines Logo
6:33 am - 2:55 pmMSN-EYW
7h 22m1 stop
American Airlines Logo
2:39 pm - 9:54 pmEYW-MSN
8h 15m1 stop
$269American Airlines
Find Deal
Wed, Nov 19 - Mon, Nov 24
American Airlines Logo
7:30 am - 4:43 pmMSN-MIA
8h 13m1 stop
American Airlines Logo
4:31 pm - 9:15 pmMIA-MSN
5h 44m1 stop
$269American Airlines
Find Deal
Sat, Sep 27 - Tue, Oct 7
United Airlines Logo
6:00 am - 2:37 pmMSN-MIA
7h 37m1 stop
United Airlines Logo
6:05 am - 2:54 pmMIA-MSN
9h 49m2 stops
$290United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
5:17 pm - 12:52 amMSN-MIA
6h 35m1 stop
Delta Logo
8:45 am - 2:36 pmMIA-MSN
6h 51m1 stop
$294Delta
Find Deal
Fri, Nov 14 - Wed, Nov 19
Delta Logo
1:20 pm - 8:12 pmMSN-EYW
5h 52m1 stop
Delta Logo
6:20 pm - 11:02 pmEYW-MSN
5h 42m1 stop
$324Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
United Airlines Logo
6:20 am - 7:08 pmMSN-MIA
11h 48m2 stops
United Airlines Logo
4:11 pm - 8:35 pmMIA-MSN
5h 24m1 stop
$327United Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 22

American Airlines flights from Madison to Florida Keys

Our best American Airlines deals on Madison to Florida Keys flight tickets
American Airlines
Nov 8
MSN6:45 amMadison Truax Field
3h 22m
MIA11:07 amMiami
Nov 15
MIA9:35 pmMiami
3h 23m
MSN11:58 pmMadison Truax Field
$249
Find similar
American Airlines
Nov 5
MSN10:21 amMadison Truax Field
7h 32m
1 stop
MIA6:53 pmMiami
Nov 8
MIA9:35 pmMiami
3h 23m
MSN11:58 pmMadison Truax Field
$259
Find similar
American Airlines
Sep 27
MSN7:30 amMadison Truax Field
8h 13m
1 stop
MIA4:43 pmMiami
Oct 7
MIA4:31 pmMiami
5h 44m
1 stop
MSN9:15 pmMadison Truax Field
$269
Find similar

Frontier flights from Madison to Florida Keys

Our best Frontier deals on Madison to Florida Keys flight tickets
Frontier
Aug 28
MSN7:59 pmMadison Truax Field
9h 31m
1 stop
MIA6:30 amMiami
Sep 4
MIA6:00 amMiami
14h 14m
1 stop
MSN7:14 pmMadison Truax Field
$258
Find similar
Frontier
Sep 19
MSN7:59 pmMadison Truax Field
27h 45m
1 stop
MIA12:44 amMiami
Sep 26
MIA6:00 amMiami
14h 14m
1 stop
MSN7:14 pmMadison Truax Field
$267
Find similar
Frontier
Aug 5
MSN7:18 pmMadison Truax Field
10h 12m
1 stop
MIA6:30 amMiami
Aug 12
MIA6:00 amMiami
13h 33m
1 stop
MSN6:33 pmMadison Truax Field
$288
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Madison to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 11/8

6:45 am-11:07 am

Nonstop3h 22m

Miami

Sat 11/15

9:35 pm-11:58 pm

Nonstop3h 23m

$249

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Thu 8/28

7:59 pm-6:30 am

1 stop9h 31m

Miami

Thu 9/4

6:00 am-7:14 pm

1 stop14h 14m

$258

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 11/5

10:21 am-6:53 pm

1 stop7h 32m

Miami

Sat 11/8

9:35 pm-11:58 pm

Nonstop3h 23m

$259

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 9/19

7:59 pm-12:44 am

1 stop27h 45m

Miami

Fri 9/26

6:00 am-7:14 pm

1 stop14h 14m

$267

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 11/19

6:33 am-2:55 pm

1 stop7h 22m

Key West

Mon 11/24

2:39 pm-9:54 pm

1 stop8h 15m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 9/27

7:30 am-4:43 pm

1 stop8h 13m

Miami

Tue 10/7

4:31 pm-9:15 pm

1 stop5h 44m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 11/8

6:00 am-2:37 pm

1 stop7h 37m

Miami

Sat 11/15

6:05 am-2:54 pm

2 stops9h 49m

$290

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 11/14

5:17 pm-12:52 am

1 stop6h 35m

Miami

Wed 11/19

8:45 am-2:36 pm

1 stop6h 51m

$294

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/23

1:20 pm-8:12 pm

1 stop5h 52m

Key West

Tue 8/26

6:20 pm-11:02 pm

1 stop5h 42m

$324

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 11/15

6:20 am-7:08 pm

2 stops11h 48m

Miami

Sat 11/22

4:11 pm-8:35 pm

1 stop5h 24m

$327

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Florida Keys from

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

What is the cheapest month to fly to Florida Keys?

The month of September is another great option to travel to Florida Keys, with average flight prices from Madison averaging around $357.

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 Thursday when prices can be found for as low as $448. The most expensive day to fly to Florida Keys is Monday, with ticket prices averaging around $1,046.

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

According to our data, the cheapest time of day to fly to Florida Keys is in the afternoon. momondo users have found flights departing from Madison to Florida Keys in the afternoon for as low as $330. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $709.

How far in advance should I book a flight 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 $442 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 $376 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

Best Price Found

$129

Fastest flight time

3h 15m

Direct flights

Sun

Airports in Florida Keys

2 airports
The best one-way flight to Florida Keys from Madison in the past 72 hours is $129. The best round-trip flight deal from Madison to Florida Keys found on momondo in the last 72 hours is $249.
The fastest flight from Madison to Florida Keys takes 3h 15m
Direct flights go from Madison to Florida Keys on Sunday. The only airline offering direct flights is American Airlines.
There are 2 airports near Florida Keys: Key West (EYW), Miami (MIA)
Search flight deals

  • 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?

  • 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?

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
DeltaPriceFrom $238Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $267Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
8,900 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.

An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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