Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Madison to Key West from $143

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 11/1. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Madison to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:11 am - 7:44 pmMSN-EYW
7h 33m1 stop
Delta Logo
6:00 pm - 10:38 pmEYW-MSN
5h 38m1 stop
$269Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
Delta Logo
10:55 am - 7:44 pmMSN-EYW
7h 49m2 stops
Delta Logo
6:00 pm - 10:38 pmEYW-MSN
5h 38m1 stop
$274Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
6:00 am - 12:33 pmMSN-EYW
5h 33m1 stop
American Airlines Logo
4:00 pm - 10:05 pmEYW-MSN
7h 05m1 stop
$276American Airlines
Find Deal
Wed, Feb 4 - Wed, Feb 11
American Airlines Logo
3:11 pm - 11:59 pmMSN-EYW
7h 48m2 stops
American Airlines Logo
6:31 am - 2:05 pmEYW-MSN
8h 34m2 stops
$279American Airlines
Find Deal
Sat, Feb 21 - Wed, Feb 25
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
$293Breeze Airways
Find Deal
Sat, Nov 8 - Tue, Nov 11
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
$298Breeze Airways
Find Deal
Sat, Nov 8 - Tue, Nov 11
Multiple Airlines Logo
6:16 pm - 2:56 pmMSN-EYW
19h 40m1 stop
Multiple Airlines Logo
3:47 pm - 9:08 amEYW-MSN
18h 21m1 stop
$335Multiple Airlines
Find Deal
Sat, Feb 7 - Fri, Feb 13
United Airlines Logo
6:15 am - 2:06 pmMSN-EYW
6h 51m1 stop
United Airlines Logo
12:22 pm - 7:05 pmEYW-MSN
7h 43m1 stop
$374United Airlines
Find Deal
Mon, Dec 15 - Sat, Dec 20
Multiple Airlines Logo
9:48 am - 11:20 amMSN-EYW
24h 32m2 stops
Multiple Airlines Logo
11:45 am - 9:08 amEYW-MSN
22h 23m1 stop
$376Multiple Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
6:30 am - 3:19 pmMSN-EYW
7h 49m1 stop
United Airlines Logo
4:00 pm - 8:35 pmEYW-MSN
5h 35m1 stop
$399United Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3

Delta flights from Madison to Key West

Our best Delta deals on Madison to Key West flight tickets
Delta
Jan 29
MSN11:11 amMadison Truax Field
7h 33m
1 stop
EYW7:44 pmKey West
Feb 2
EYW6:00 pmKey West
5h 38m
1 stop
MSN10:38 pmMadison Truax Field
$269
Find similar
Delta
Jan 29
MSN10:55 amMadison Truax Field
7h 49m
2 stops
EYW7:44 pmKey West
Feb 2
EYW6:00 pmKey West
5h 38m
1 stop
MSN10:38 pmMadison Truax Field
$274
Find similar
Delta
Feb 4
MSN11:11 amMadison Truax Field
7h 33m
1 stop
EYW7:44 pmKey West
Feb 11
EYW1:30 pmKey West
7h 45m
1 stop
MSN8:15 pmMadison Truax Field
$319
Find similar

American Airlines flights from Madison to Key West

Our best American Airlines deals on Madison to Key West flight tickets
American Airlines
Feb 4
MSN6:00 amMadison Truax Field
5h 33m
1 stop
EYW12:33 pmKey West
Feb 11
EYW4:00 pmKey West
7h 05m
1 stop
MSN10:05 pmMadison Truax Field
$276
Find similar
American Airlines
Feb 21
MSN3:11 pmMadison Truax Field
7h 48m
2 stops
EYW11:59 pmKey West
Feb 25
EYW6:31 amKey West
8h 34m
2 stops
MSN2:05 pmMadison Truax Field
$279
Find similar
American Airlines
Nov 19
MSN6:00 amMadison Truax Field
8h 28m
1 stop
EYW3:28 pmKey West
Nov 24
EYW6:33 pmKey West
5h 57m
1 stop
MSN11:30 pmMadison Truax Field
$294
Find similar

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 October 16, 2025.
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

Thu 1/29

11:11 am-7:44 pm

1 stop7h 33m

Key West

Mon 2/2

6:00 pm-10:38 pm

1 stop5h 38m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 1/29

10:55 am-7:44 pm

2 stops7h 49m

Key West

Mon 2/2

6:00 pm-10:38 pm

1 stop5h 38m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 2/4

6:00 am-12:33 pm

1 stop5h 33m

Key West

Wed 2/11

4:00 pm-10:05 pm

1 stop7h 05m

$276

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 2/21

3:11 pm-11:59 pm

2 stops7h 48m

Key West

Wed 2/25

6:31 am-2:05 pm

2 stops8h 34m

$279

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 11/8

6:08 pm-8:15 am

1 stop13h 07m

Key West

Tue 11/11

11:45 am-9:08 am

1 stop22h 23m

$293

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 11/8

6:08 pm-8:15 am

1 stop13h 07m

Key West

Tue 11/11

11:45 am-9:08 am

1 stop22h 23m

$298

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 2/7

6:16 pm-2:56 pm

1 stop19h 40m

Key West

Fri 2/13

3:47 pm-9:08 am

1 stop18h 21m

$335

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 12/15

6:15 am-2:06 pm

1 stop6h 51m

Key West

Sat 12/20

12:22 pm-7:05 pm

1 stop7h 43m

$374

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 11/8

9:48 am-11:20 am

2 stops24h 32m

Key West

Tue 11/11

11:45 am-9:08 am

1 stop22h 23m

$376

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 10/30

6:30 am-3:19 pm

1 stop7h 49m

Key West

Mon 11/3

4:00 pm-8:35 pm

1 stop5h 35m

$399

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Madison and Key West?

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 October is also very affordable. Most momondo users find prices during this month for around $375.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Madison is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $376. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Madison to Key West for around $548.

What is the cheapest time of day to depart on your flight to Key West?

According to our data, the cheapest time of day to fly to Key West is at noon. momondo users have found flights departing from Madison to Key West at noon for as low as $313. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the morning, with an average ticket price of $441. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

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 $444 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 $354 on momondo.

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

Direct flights

None
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 11m.

  • 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 $267Free CancellationRating
7.9
7,984 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $348Free CancellationRating
7.4
8,982 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/15
Sat 11/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States