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Cheap flights from Madison to Florida Keys from $78

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 11/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Florida Keys

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:04 pm - 5:10 amMSN-MIA
13h 06m1 stop
Frontier Logo
6:15 am - 2:25 pmMIA-MSN
9h 10m1 stop
$144Frontier
Find Deal
Sat, Nov 22 - Mon, Nov 24
Frontier Logo
3:04 pm - 5:10 amMSN-MIA
13h 06m1 stop
Frontier Logo
6:15 am - 3:29 pmMIA-MSN
10h 14m1 stop
$223Frontier
Find Deal
Sat, Nov 22 - Wed, Nov 26
Multiple Airlines Logo
6:08 pm - 2:25 pmMSN-MIA
19h 17m2 stops
Multiple Airlines Logo
6:15 am - 2:25 pmMIA-MSN
9h 10m1 stop
$237Multiple Airlines
Find Deal
Wed, Nov 19 - Mon, Nov 24
Delta Logo
11:15 am - 5:13 pmMSN-EYW
4h 58m1 stop
Delta Logo
6:07 pm - 10:37 pmEYW-MSN
5h 30m1 stop
$269Delta
Find Deal
Fri, Feb 6 - Fri, Feb 13
United Airlines Logo
2:56 pm - 10:15 pmMSN-MIA
6h 19m1 stop
United Airlines Logo
4:54 pm - 11:44 pmMIA-MSN
7h 50m1 stop
$269United Airlines
Find Deal
Sun, Feb 1 - Sat, Feb 7
Delta Logo
9:42 am - 7:42 pmMSN-EYW
9h 00m2 stops
Delta Logo
6:08 pm - 10:37 pmEYW-MSN
5h 29m1 stop
$274Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
United Airlines Logo
2:29 pm - 10:10 pmMSN-MIA
6h 41m1 stop
United Airlines Logo
7:15 am - 4:51 pmMIA-MSN
10h 36m2 stops
$274United Airlines
Find Deal
Sat, Jan 3 - Sat, Jan 10
American Airlines Logo
6:27 am - 3:15 pmMSN-EYW
7h 48m1 stop
American Airlines Logo
3:06 pm - 9:18 pmEYW-MSN
7h 12m1 stop
$276American Airlines
Find Deal
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
1:16 pm - 9:47 pmMSN-EYW
7h 31m2 stops
American Airlines Logo
6:06 am - 3:27 pmEYW-MSN
10h 21m2 stops
$279American Airlines
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Fri, Feb 6 - Wed, Feb 11
Multiple Airlines Logo
2:35 pm - 11:22 amMSN-MIA
19h 47m2 stops
Multiple Airlines Logo
6:15 am - 2:25 pmMIA-MSN
9h 10m1 stop
$291Multiple Airlines
Find Deal
Sun, Nov 16 - Mon, Nov 24

Frontier flights from Madison to Florida Keys

Our best Frontier deals on Madison to Florida Keys flight tickets
Frontier
Nov 22
MSN3:04 pmMadison Truax Field
13h 06m
1 stop
MIA5:10 amMiami
Nov 24
MIA6:15 amMiami
9h 10m
1 stop
MSN2:25 pmMadison Truax Field
$144
Find similar
Frontier
Nov 22
MSN3:04 pmMadison Truax Field
13h 06m
1 stop
MIA5:10 amMiami
Nov 26
MIA6:15 amMiami
10h 14m
1 stop
MSN3:29 pmMadison Truax Field
$223
Find similar
Frontier
Nov 22
MSN3:04 pmMadison Truax Field
18h 45m
2 stops
MIA10:49 amMiami
Nov 24
MIA6:15 amMiami
9h 10m
1 stop
MSN2:25 pmMadison Truax Field
$233
Find similar

United Airlines flights from Madison to Florida Keys

Our best United Airlines deals on Madison to Florida Keys flight tickets
United Airlines
Feb 1
MSN2:56 pmMadison Truax Field
6h 19m
1 stop
MIA10:15 pmMiami
Feb 7
MIA4:54 pmMiami
7h 50m
1 stop
MSN11:44 pmMadison Truax Field
$269
Find similar
United Airlines
Jan 3
MSN2:29 pmMadison Truax Field
6h 41m
1 stop
MIA10:10 pmMiami
Jan 12
MIA11:05 amMiami
9h 02m
2 stops
MSN7:07 pmMadison Truax Field
$274
Find similar
United Airlines
Jan 3
MSN2:29 pmMadison Truax Field
6h 41m
1 stop
MIA10:10 pmMiami
Jan 12
MIA4:19 pmMiami
5h 46m
1 stop
MSN9:05 pmMadison Truax Field
$293
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 November 6, 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 11/22

3:04 pm-5:10 am

1 stop13h 06m

Miami

Mon 11/24

6:15 am-2:25 pm

1 stop9h 10m

$144

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 11/22

3:04 pm-5:10 am

1 stop13h 06m

Miami

Wed 11/26

6:15 am-3:29 pm

1 stop10h 14m

$223

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Wed 11/19

6:08 pm-2:25 pm

2 stops19h 17m

Miami

Mon 11/24

6:15 am-2:25 pm

1 stop9h 10m

$237

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

11:15 am-5:13 pm

1 stop4h 58m

Key West

Fri 2/13

6:07 pm-10:37 pm

1 stop5h 30m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 2/1

2:56 pm-10:15 pm

1 stop6h 19m

Miami

Sat 2/7

4:54 pm-11:44 pm

1 stop7h 50m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 1/29

9:42 am-7:42 pm

2 stops9h 00m

Key West

Mon 2/2

6:08 pm-10:37 pm

1 stop5h 29m

$274

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 1/3

2:29 pm-10:10 pm

1 stop6h 41m

Miami

Sat 1/10

7:15 am-4:51 pm

2 stops10h 36m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/25

6:27 am-3:15 pm

1 stop7h 48m

Key West

Wed 4/29

3:06 pm-9:18 pm

1 stop7h 12m

$276

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

1:16 pm-9:47 pm

2 stops7h 31m

Key West

Wed 2/11

6:06 am-3:27 pm

2 stops10h 21m

$279

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sun 11/16

2:35 pm-11:22 am

2 stops19h 47m

Miami

Mon 11/24

6:15 am-2:25 pm

1 stop9h 10m

$291

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 October is another great option to travel to Florida Keys, with average flight prices from Madison averaging around $407.

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 $698.

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 $375 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

1 airport
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 is 1 airport near Florida Keys: 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
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
DeltaPriceFrom $293Free CancellationRating
7.9
8,004 reviews
Search Delta flights
United AirlinesPriceFrom $348Free CancellationRating
7.4
9,003 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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