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Cheap flights from Madison to Key West from $195

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 8/8. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
6:50 pm - 7:13 pm
MSN
-
EYW
47h 23m
2 stops
Breeze Airways Logo
1:11 pm - 9:47 am
EYW
-
MSN
21h 36m
1 stop
$272Breeze Airways
Fri, Aug 28 - Fri, Sep 4
American Airlines Logo
6:30 am - 12:55 pm
MSN
-
EYW
5h 25m
1 stop
American Airlines Logo
4:50 pm - 11:09 pm
EYW
-
MSN
7h 19m
1 stop
$323American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
7:00 am - 4:11 pm
MSN
-
EYW
8h 11m
1 stop
American Airlines Logo
4:50 pm - 11:09 pm
EYW
-
MSN
7h 19m
1 stop
$326American Airlines
Fri, Jul 31 - Wed, Aug 5
American Airlines Logo
7:00 am - 4:11 pm
MSN
-
EYW
8h 11m
1 stop
American Airlines Logo
7:33 pm - 11:59 pm
EYW
-
MSN
5h 26m
1 stop
$329American Airlines
Wed, Jul 29 - Mon, Aug 3
Breeze Airways Logo
7:55 pm - 11:25 am
MSN
-
EYW
14h 30m
1 stop
Breeze Airways Logo
1:14 pm - 9:47 am
EYW
-
MSN
21h 33m
1 stop
$341Breeze Airways
Sat, Jul 25 - Tue, Jul 28
Breeze Airways Logo
7:55 pm - 11:25 am
MSN
-
EYW
14h 30m
1 stop
Breeze Airways Logo
11:46 am - 8:25 am
EYW
-
MSN
45h 39m
2 stops
$345Breeze Airways
Sat, Jul 25 - Wed, Jul 29
Breeze Airways Logo
7:55 pm - 11:25 am
MSN
-
EYW
14h 30m
1 stop
Breeze Airways Logo
1:14 pm - 9:47 am
EYW
-
MSN
21h 33m
1 stop
$353Breeze Airways
Sat, Aug 1 - Tue, Aug 4
American Airlines Logo
9:18 am - 3:50 pm
MSN
-
EYW
5h 32m
1 stop
American Airlines Logo
7:33 pm - 11:42 pm
EYW
-
MSN
5h 09m
1 stop
$364American Airlines
Fri, Jul 17 - Wed, Jul 22
American Airlines Logo
6:30 am - 12:55 pm
MSN
-
EYW
5h 25m
1 stop
American Airlines Logo
4:50 pm - 11:09 pm
EYW
-
MSN
7h 19m
1 stop
$376American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
8:25 am - 4:11 pm
MSN
-
EYW
6h 46m
1 stop
American Airlines Logo
7:19 pm - 11:57 pm
EYW
-
MSN
5h 38m
1 stop
$379American Airlines
Tue, Oct 13 - Sat, Oct 17

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Breeze Airways flights from Madison to Key West

Our best Breeze Airways deals on Madison to Key West flight tickets
Breeze Airways
Aug 28
MSN6:50 pmMadison Truax Field
47h 23m
2 stops
EYW7:13 pmKey West
Sep 4
EYW1:11 pmKey West
21h 36m
1 stop
MSN9:47 amMadison Truax Field
$272
Breeze Airways
Jul 25
MSN7:55 pmMadison Truax Field
14h 30m
1 stop
EYW11:25 amKey West
Jul 28
EYW1:14 pmKey West
21h 33m
1 stop
MSN9:47 amMadison Truax Field
$341
Breeze Airways
Jul 25
MSN7:55 pmMadison Truax Field
14h 30m
1 stop
EYW11:25 amKey West
Jul 29
EYW11:46 amKey West
45h 39m
2 stops
MSN8:25 amMadison Truax Field
$345

American Airlines flights from Madison to Key West

Our best American Airlines deals on Madison to Key West flight tickets
American Airlines
Aug 12
MSN6:30 amMadison Truax Field
5h 25m
1 stop
EYW12:55 pmKey West
Aug 19
EYW4:50 pmKey West
7h 19m
1 stop
MSN11:09 pmMadison Truax Field
$323
American Airlines
Jul 31
MSN7:00 amMadison Truax Field
8h 11m
1 stop
EYW4:11 pmKey West
Aug 5
EYW4:50 pmKey West
7h 19m
1 stop
MSN11:09 pmMadison Truax Field
$326
American Airlines
Jul 29
MSN7:00 amMadison Truax Field
8h 11m
1 stop
EYW4:11 pmKey West
Aug 3
EYW7:33 pmKey West
5h 26m
1 stop
MSN11:59 pmMadison Truax Field
$329

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 July 5, 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

Cheapest round-trip

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 8/28

6:50 pm-7:13 pm

2 stops47h 23m

Key West

Fri 9/4

1:11 pm-9:47 am

1 stop21h 36m

$272

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 8/12

6:30 am-12:55 pm

1 stop5h 25m

Key West

Wed 8/19

4:50 pm-11:09 pm

1 stop7h 19m

$323

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/31

7:00 am-4:11 pm

1 stop8h 11m

Key West

Wed 8/5

4:50 pm-11:09 pm

1 stop7h 19m

$326

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 7/29

7:00 am-4:11 pm

1 stop8h 11m

Key West

Mon 8/3

7:33 pm-11:59 pm

1 stop5h 26m

$329

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 7/25

7:55 pm-11:25 am

1 stop14h 30m

Key West

Tue 7/28

1:14 pm-9:47 am

1 stop21h 33m

$341

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 7/25

7:55 pm-11:25 am

1 stop14h 30m

Key West

Wed 7/29

11:46 am-8:25 am

2 stops45h 39m

$345

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/1

7:55 pm-11:25 am

1 stop14h 30m

Key West

Tue 8/4

1:14 pm-9:47 am

1 stop21h 33m

$353
Quickest round-trip

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/17

9:18 am-3:50 pm

1 stop5h 32m

Key West

Wed 7/22

7:33 pm-11:42 pm

1 stop5h 09m

$364

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 8/12

6:30 am-12:55 pm

1 stop5h 25m

Key West

Wed 8/19

4:50 pm-11:09 pm

1 stop7h 19m

$376

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 10/13

8:25 am-4:11 pm

1 stop6h 46m

Key West

Sat 10/17

7:19 pm-11:57 pm

1 stop5h 38m

$379

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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, September 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 $0. If you are unable to visit Key West during the month of September, then departing from Madison during the month July is also very affordable. Most momondo users find prices during this month for around $0.

How far in advance should I book a flight from Madison 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 $433 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 $330 on momondo.

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

You could potentially save up to 48% 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

4h 48m

Direct flights

None
The fastest flight from Madison to Key West takes 4h 48m
There are no direct flights from Madison to Key West. There are no popular flight routes from Madison to Key West.
Search flight deals

Frequently asked questions about flying from Madison to Key West

  • 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 4h 48m.

  • 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
American AirlinesPriceFrom $282Free CancellationRating
7.1
11,777 reviews
Search American Airlines flights
DeltaPriceFrom $302Free CancellationRating
7.8
8,451 reviews
Search Delta flights
United AirlinesPriceFrom $313Free CancellationRating
7.4
9,933 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

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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