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Cheap flights from Madison to Florida Keys from $148

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 11/17. 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

American Airlines Logo
12:19 pm - 6:35 pmMSN-EYW
5h 16m1 stop
American Airlines Logo
5:24 pm - 11:42 pmEYW-MSN
7h 18m1 stop
$269American Airlines
Find Deal
Fri, Jan 30 - Tue, Feb 3
United Airlines Logo
6:30 am - 3:11 pmMSN-MIA
7h 41m1 stop
United Airlines Logo
4:56 pm - 10:33 pmMIA-MSN
6h 37m1 stop
$269United Airlines
Find Deal
Sat, Oct 18 - Fri, Oct 24
American Airlines Logo
12:19 pm - 6:35 pmMSN-EYW
5h 16m1 stop
American Airlines Logo
8:10 am - 3:04 pmEYW-MSN
7h 54m2 stops
$274American Airlines
Find Deal
Fri, Jan 30 - Tue, Feb 3
United Airlines Logo
10:51 am - 9:01 pmMSN-MIA
9h 10m2 stops
United Airlines Logo
4:56 pm - 10:33 pmMIA-MSN
6h 37m1 stop
$274United Airlines
Find Deal
Sat, Oct 18 - Fri, Oct 24
Frontier Logo
7:59 pm - 6:19 amMSN-MIA
9h 20m1 stop
Frontier Logo
6:00 am - 7:15 pmMIA-MSN
14h 15m1 stop
$276Frontier
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Fri, Oct 24 - Fri, Oct 31
Delta Logo
5:28 am - 11:21 amMSN-MIA
4h 53m1 stop
Delta Logo
6:00 am - 10:32 amMIA-MSN
5h 32m1 stop
$289Delta
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Mon, Dec 15 - Tue, Dec 23
Delta Logo
7:00 am - 7:44 pmMSN-EYW
11h 44m2 stops
Delta Logo
1:30 pm - 8:15 pmEYW-MSN
7h 45m1 stop
$299Delta
Find Deal
Wed, Feb 25 - Tue, Mar 3
Frontier Logo
7:59 pm - 11:23 pmMSN-MIA
26h 24m2 stops
Frontier Logo
6:00 am - 7:15 pmMIA-MSN
14h 15m1 stop
$318Frontier
Find Deal
Fri, Oct 24 - Fri, Oct 31
Breeze Airways Logo
6:08 pm - 8:15 amMSN-EYW
13h 07m1 stop
Breeze Airways Logo
11:45 am - 9:08 amEYW-MSN
22h 23m1 stop
$320Breeze Airways
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Wed, Oct 22 - Tue, Oct 28
Breeze Airways Logo
9:48 am - 10:21 amMSN-EYW
23h 33m1 stop
Breeze Airways Logo
9:49 am - 9:08 amEYW-MSN
24h 19m1 stop
$332Breeze Airways
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Sat, Jan 31 - Fri, Feb 6

United Airlines flights from Madison to Florida Keys

Our best United Airlines deals on Madison to Florida Keys flight tickets
United Airlines
Oct 18
MSN6:30 amMadison Truax Field
7h 41m
1 stop
MIA3:11 pmMiami
Oct 24
MIA4:56 pmMiami
6h 37m
1 stop
MSN10:33 pmMadison Truax Field
$269
Find similar
United Airlines
Oct 18
MSN10:51 amMadison Truax Field
9h 10m
2 stops
MIA9:01 pmMiami
Oct 24
MIA4:56 pmMiami
6h 37m
1 stop
MSN10:33 pmMadison Truax Field
$274
Find similar
United Airlines
Mar 10
MSN2:25 pmMadison Truax Field
6h 51m
1 stop
MIA10:16 pmMiami
Mar 16
MIA7:25 amMiami
5h 28m
1 stop
MSN11:53 amMadison Truax Field
$330
Find similar

Frontier flights from Madison to Florida Keys

Our best Frontier deals on Madison to Florida Keys flight tickets
Frontier
Oct 24
MSN7:59 pmMadison Truax Field
9h 20m
1 stop
MIA6:19 amMiami
Oct 31
MIA6:00 amMiami
14h 15m
1 stop
MSN7:15 pmMadison Truax Field
$276
Find similar
Frontier
Sep 25
MSN7:59 pmMadison Truax Field
27h 45m
1 stop
MIA12:44 amMiami
Sep 28
MIA6:00 amMiami
14h 14m
1 stop
MSN7:14 pmMadison Truax Field
$280
Find similar
Frontier
Oct 24
MSN7:59 pmMadison Truax Field
26h 24m
2 stops
MIA11:23 pmMiami
Oct 31
MIA6:00 amMiami
14h 15m
1 stop
MSN7:15 pmMadison Truax Field
$318
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 September 18, 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

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 1/30

12:19 pm-6:35 pm

1 stop5h 16m

Key West

Tue 2/3

5:24 pm-11:42 pm

1 stop7h 18m

$269

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 10/18

6:30 am-3:11 pm

1 stop7h 41m

Miami

Fri 10/24

4:56 pm-10:33 pm

1 stop6h 37m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 1/30

12:19 pm-6:35 pm

1 stop5h 16m

Key West

Tue 2/3

8:10 am-3:04 pm

2 stops7h 54m

$274

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Sat 10/18

10:51 am-9:01 pm

2 stops9h 10m

Miami

Fri 10/24

4:56 pm-10:33 pm

1 stop6h 37m

$274

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 10/24

7:59 pm-6:19 am

1 stop9h 20m

Miami

Fri 10/31

6:00 am-7:15 pm

1 stop14h 15m

$276

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Mon 12/15

5:28 am-11:21 am

1 stop4h 53m

Miami

Tue 12/23

6:00 am-10:32 am

1 stop5h 32m

$289

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 2/25

7:00 am-7:44 pm

2 stops11h 44m

Key West

Tue 3/3

1:30 pm-8:15 pm

1 stop7h 45m

$299

MadisonMiami

MSN - MIA

MSNMIA

Madison Truax Field

Fri 10/24

7:59 pm-11:23 pm

2 stops26h 24m

Miami

Fri 10/31

6:00 am-7:15 pm

1 stop14h 15m

$318

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 10/22

6:08 pm-8:15 am

1 stop13h 07m

Key West

Tue 10/28

11:45 am-9:08 am

1 stop22h 23m

$320

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 1/31

9:48 am-10:21 am

1 stop23h 33m

Key West

Fri 2/6

9:49 am-9:08 am

1 stop24h 19m

$332

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 January is another great option to travel to Florida Keys, with average flight prices from Madison averaging around $397.

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 $680.

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 $450 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 $393 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
DeltaPriceFrom $238Free CancellationRating
7.9
7,964 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $288Free CancellationRating
7.4
8,926 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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