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Cheap flights from Madison to Key West from $249

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 Key West departing on 2/21. 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 Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:35 am - 10:57 pm
MSN
-
EYW
10h 22m
2 stops
American Airlines Logo
2:14 pm - 11:14 pm
EYW
-
MSN
10h 00m
1 stop
$288American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
11:35 am - 10:57 pm
MSN
-
EYW
10h 22m
2 stops
American Airlines Logo
3:58 pm - 11:14 pm
EYW
-
MSN
8h 16m
2 stops
$294American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
7:00 am - 1:26 pm
MSN
-
EYW
5h 26m
1 stop
American Airlines Logo
6:49 pm - 11:22 pm
EYW
-
MSN
5h 33m
1 stop
$314American Airlines
Mon, Mar 2 - Mon, Mar 16
American Airlines Logo
11:35 am - 10:57 pm
MSN
-
EYW
10h 22m
2 stops
American Airlines Logo
5:42 pm - 11:28 pm
EYW
-
MSN
6h 46m
1 stop
$316American Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
7:00 am - 4:49 pm
MSN
-
EYW
8h 49m
2 stops
American Airlines Logo
6:49 pm - 11:22 pm
EYW
-
MSN
5h 33m
1 stop
$319American Airlines
Mon, Mar 2 - Mon, Mar 16
American Airlines Logo
11:35 am - 10:57 pm
MSN
-
EYW
10h 22m
2 stops
American Airlines Logo
6:45 am - 2:46 pm
EYW
-
MSN
9h 01m
2 stops
$322American Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
6:01 am - 3:23 pm
MSN
-
EYW
8h 22m
1 stop
American Airlines Logo
4:20 pm - 11:55 pm
EYW
-
MSN
8h 35m
1 stop
$336American Airlines
Sat, Apr 25 - Wed, Apr 29
Breeze Airways Logo
6:36 pm - 9:06 am
MSN
-
EYW
13h 30m
1 stop
Breeze Airways Logo
11:51 am - 5:56 pm
EYW
-
MSN
7h 05m
1 stop
$338Breeze Airways
Sat, Apr 11 - Wed, Apr 15
United Airlines Logo
2:48 pm - 10:09 pm
MSN
-
EYW
6h 21m
1 stop
United Airlines Logo
3:56 pm - 9:07 pm
EYW
-
MSN
6h 11m
1 stop
$341United Airlines
Sat, Feb 21 - Wed, Feb 25
American Airlines Logo
11:35 am - 10:57 pm
MSN
-
EYW
10h 22m
2 stops
American Airlines Logo
3:58 pm - 11:56 pm
EYW
-
MSN
8h 58m
2 stops
$383American Airlines
Thu, Apr 23 - Sat, May 2

American Airlines flights from Madison to Key West

Our best American Airlines deals on Madison to Key West flight tickets
American Airlines
Apr 25
MSN11:35 amMadison Truax Field
10h 22m
2 stops
EYW10:57 pmKey West
Apr 29
EYW2:14 pmKey West
10h 00m
1 stop
MSN11:14 pmMadison Truax Field
$288
American Airlines
Apr 25
MSN11:35 amMadison Truax Field
10h 22m
2 stops
EYW10:57 pmKey West
Apr 29
EYW3:58 pmKey West
8h 16m
2 stops
MSN11:14 pmMadison Truax Field
$294
American Airlines
Mar 2
MSN7:00 amMadison Truax Field
5h 26m
1 stop
EYW1:26 pmKey West
Mar 16
EYW6:49 pmKey West
5h 33m
1 stop
MSN11:22 pmMadison Truax Field
$314

United Airlines flights from Madison to Key West

Our best United Airlines deals on Madison to Key West flight tickets
United Airlines
Feb 21
MSN2:48 pmMadison Truax Field
6h 21m
1 stop
EYW10:09 pmKey West
Feb 25
EYW3:56 pmKey West
6h 11m
1 stop
MSN9:07 pmMadison Truax Field
$341
United Airlines
Jan 24
MSN8:15 amMadison Truax Field
6h 02m
1 stop
EYW3:17 pmKey West
Jan 27
EYW4:15 pmKey West
5h 50m
1 stop
MSN9:05 pmMadison Truax Field
$389
United Airlines
Jan 24
MSN6:30 amMadison Truax Field
8h 52m
2 stops
EYW4:22 pmKey West
Jan 27
EYW4:15 pmKey West
5h 50m
1 stop
MSN9:05 pmMadison Truax Field
$394

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Key West 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 January 20, 2026.
Use the filters below to find and compare flights from Madison to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/25

11:35 am-10:57 pm

2 stops10h 22m

Key West

Wed 4/29

2:14 pm-11:14 pm

1 stop10h 00m

$288

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/25

11:35 am-10:57 pm

2 stops10h 22m

Key West

Wed 4/29

3:58 pm-11:14 pm

2 stops8h 16m

$294

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 3/2

7:00 am-1:26 pm

1 stop5h 26m

Key West

Mon 3/16

6:49 pm-11:22 pm

1 stop5h 33m

$314

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

11:35 am-10:57 pm

2 stops10h 22m

Key West

Wed 4/15

5:42 pm-11:28 pm

1 stop6h 46m

$316

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 3/2

7:00 am-4:49 pm

2 stops8h 49m

Key West

Mon 3/16

6:49 pm-11:22 pm

1 stop5h 33m

$319

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

11:35 am-10:57 pm

2 stops10h 22m

Key West

Wed 4/15

6:45 am-2:46 pm

2 stops9h 01m

$322

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/25

6:01 am-3:23 pm

1 stop8h 22m

Key West

Wed 4/29

4:20 pm-11:55 pm

1 stop8h 35m

$336

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

6:36 pm-9:06 am

1 stop13h 30m

Key West

Wed 4/15

11:51 am-5:56 pm

1 stop7h 05m

$338

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 2/21

2:48 pm-10:09 pm

1 stop6h 21m

Key West

Wed 2/25

3:56 pm-9:07 pm

1 stop6h 11m

$341

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 4/23

11:35 am-10:57 pm

2 stops10h 22m

Key West

Sat 5/2

3:58 pm-11:56 pm

2 stops8h 58m

$383

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 Key West from

How to get the cheapest flight ticket from Madison to Key West

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 Key West?

In general, August is the cheapest month to fly from Madison to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $333. If you are unable to visit Key West during the month of August, then departing from Madison during the month April is also very affordable. Most momondo users find prices during this month for around $368.

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $429 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Madison for as low as $348 on momondo.

Can stopping save me money on Madison to Key West flights?

You could potentially save up to 14% on your flight if you consider stops on a Madison to Key West flight.

When to book flights from Madison to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to Key West (MSN to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Key West

Fastest flight time

5h 16m

Direct flights

None
The fastest flight from Madison to Key West takes 5h 16m
There are no direct flights from Madison to Key West. There are no popular flight routes from Madison to Key West.
Search flight deals

  • How far is Madison Truax Field to Key West by plane?

    There are 1349.4 mi between Madison Truax Field and Key West. In terms of flight time, this usually takes a little over 5h 16m.

  • When did momondo last update prices for flights from Madison Truax Field Airport to Key West Airport?

    Prices for flights from Madison Truax Field Airport to Key West Airport are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Key West Airport?

  • How old do you have to be to fly from Madison Truax Field Airport to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Madison Truax Field Airport to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Madison to Key West?

Best airlines flying from Madison to Key West

Compare and see reviews for airlines that fly from Madison to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $254Free CancellationRating
7.9
8,080 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,164 reviews
Search American Airlines flights
United AirlinesPriceFrom $312Free CancellationRating
7.4
9,183 reviews
Search United Airlines flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Key West?

It is quick and easy to find Madison to Key West flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Key West that suits you.

Can I find flights from Madison to Key West with flexible booking policies on momondo?

momondo does allow users to show only those flights to Key West from Madison which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Madison to Key West?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Madison to Key West.

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

Yes. momondo can track prices for Madison to Key West flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Key West trip

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