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Cheap flights from Key West to Madison from $258

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Madison departing on 8/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Key West to Madison

Cheap round-trip flights

Delta Logo
6:22 pm - 10:48 pmEYW-MSN
5h 26m1 stop
Delta Logo
5:40 am - 1:05 pmMSN-EYW
6h 25m1 stop
$269Delta
Find Deal
Wed, Aug 20 - Mon, Sep 1
American Airlines Logo
4:49 pm - 11:59 pmEYW-MSN
8h 10m1 stop
American Airlines Logo
6:46 am - 4:22 pmMSN-EYW
8h 36m1 stop
$294American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
1:29 pm - 11:02 pmEYW-MSN
10h 33m2 stops
American Airlines Logo
6:46 am - 4:22 pmMSN-EYW
8h 36m1 stop
$299American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
1:52 pm - 11:27 pmEYW-MSN
10h 35m2 stops
American Airlines Logo
6:19 am - 7:07 pmMSN-EYW
11h 48m2 stops
$304American Airlines
Find Deal
Wed, Aug 20 - Mon, Sep 1
American Airlines Logo
4:49 pm - 11:59 pmEYW-MSN
8h 10m1 stop
American Airlines Logo
6:46 am - 4:22 pmMSN-EYW
8h 36m1 stop
$376American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
4:49 pm - 11:59 pmEYW-MSN
8h 10m1 stop
American Airlines Logo
6:46 am - 7:07 pmMSN-EYW
11h 21m2 stops
$381American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
1:29 pm - 11:59 pmEYW-MSN
11h 30m2 stops
American Airlines Logo
5:30 am - 4:46 pmMSN-EYW
10h 16m2 stops
$386American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
United Airlines Logo
3:05 pm - 10:45 pmEYW-MSN
8h 40m1 stop
United Airlines Logo
9:30 pm - 3:19 pmMSN-EYW
16h 49m1 stop
$513United Airlines
Find Deal
Tue, Nov 25 - Sun, Nov 30
United Airlines Logo
3:05 pm - 2:03 pmEYW-MSN
23h 58m2 stops
United Airlines Logo
9:30 pm - 3:19 pmMSN-EYW
16h 49m1 stop
$582United Airlines
Find Deal
Tue, Nov 25 - Sun, Nov 30
United Airlines Logo
3:41 pm - 3:02 pmEYW-MSN
24h 21m3 stops
United Airlines Logo
6:30 am - 2:25 pmMSN-EYW
30h 55m2 stops
$948United Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25

American Airlines flights from Key West to Madison

Our best American Airlines deals on Key West to Madison flight tickets
American Airlines
Aug 21
EYW4:49 pmKey West
8h 10m
1 stop
MSN11:59 pmMadison Truax Field
Aug 25
MSN6:46 amMadison Truax Field
8h 36m
1 stop
EYW4:22 pmKey West
$294
Find similar
American Airlines
Aug 21
EYW1:29 pmKey West
10h 33m
2 stops
MSN11:02 pmMadison Truax Field
Aug 25
MSN6:46 amMadison Truax Field
8h 36m
1 stop
EYW4:22 pmKey West
$299
Find similar
American Airlines
Aug 20
EYW1:52 pmKey West
10h 35m
2 stops
MSN11:27 pmMadison Truax Field
Sep 1
MSN6:19 amMadison Truax Field
11h 48m
2 stops
EYW7:07 pmKey West
$304
Find similar

United Airlines flights from Key West to Madison

Our best United Airlines deals on Key West to Madison flight tickets
United Airlines
Nov 25
EYW3:05 pmKey West
8h 40m
1 stop
MSN10:45 pmMadison Truax Field
Nov 30
MSN9:30 pmMadison Truax Field
16h 49m
1 stop
EYW3:19 pmKey West
$513
Find similar
United Airlines
Nov 25
EYW3:05 pmKey West
23h 58m
2 stops
MSN2:03 pmMadison Truax Field
Nov 30
MSN9:30 pmMadison Truax Field
16h 49m
1 stop
EYW3:19 pmKey West
$582
Find similar
United Airlines
Aug 21
EYW3:41 pmKey West
24h 21m
3 stops
MSN3:02 pmMadison Truax Field
Aug 25
MSN6:30 amMadison Truax Field
30h 55m
2 stops
EYW2:25 pmKey West
$948
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Madison 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 31, 2025.
Use the filters below to find and compare flights from Key West to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 8/20

6:22 pm-10:48 pm

1 stop5h 26m

Madison Truax Field

Mon 9/1

5:40 am-1:05 pm

1 stop6h 25m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

4:49 pm-11:59 pm

1 stop8h 10m

Madison Truax Field

Mon 8/25

6:46 am-4:22 pm

1 stop8h 36m

$294

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

1:29 pm-11:02 pm

2 stops10h 33m

Madison Truax Field

Mon 8/25

6:46 am-4:22 pm

1 stop8h 36m

$299

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 8/20

1:52 pm-11:27 pm

2 stops10h 35m

Madison Truax Field

Mon 9/1

6:19 am-7:07 pm

2 stops11h 48m

$304

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

4:49 pm-11:59 pm

1 stop8h 10m

Madison Truax Field

Mon 8/25

6:46 am-4:22 pm

1 stop8h 36m

$376

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

4:49 pm-11:59 pm

1 stop8h 10m

Madison Truax Field

Mon 8/25

6:46 am-7:07 pm

2 stops11h 21m

$381

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

1:29 pm-11:59 pm

2 stops11h 30m

Madison Truax Field

Mon 8/25

5:30 am-4:46 pm

2 stops10h 16m

$386

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 11/25

3:05 pm-10:45 pm

1 stop8h 40m

Madison Truax Field

Sun 11/30

9:30 pm-3:19 pm

1 stop16h 49m

$513

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 11/25

3:05 pm-2:03 pm

2 stops23h 58m

Madison Truax Field

Sun 11/30

9:30 pm-3:19 pm

1 stop16h 49m

$582

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 8/21

3:41 pm-3:02 pm

3 stops24h 21m

Madison Truax Field

Mon 8/25

6:30 am-2:25 pm

2 stops30h 55m

$948

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Madison from

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

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 day to depart on your flight to Madison?

The cheapest day to depart from Key West to Madison is on a Friday when prices can be found for as low as $293. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $817.

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

According to our data, the cheapest time of day to fly to Madison is in the afternoon. momondo users have found flights departing from Key West to Madison in the afternoon for as low as $377. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is at noon when prices are around $475.

When to book flights from Key West to Madison

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

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

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

Best Price Found

$258

Fastest flight time

5h 26m

Direct flights

None

Airports in Madison

1 airport
The best one-way flight to Madison from Key West in the past 72 hours is $258. The best round-trip flight deal from Key West to Madison found on momondo in the last 72 hours is $269.
The fastest flight from Key West to Madison takes 5h 26m
There are no direct flights from Key West to Madison. Popular non-direct route for this connection is Key West Airport - Madison Truax Field Airport.
There is 1 airport near Madison: Madison Truax Field (MSN)
Search flight deals

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

    A flight from Key West to Madison Truax Field will travel around 1349.4 mi. In terms of flight time, this usually takes a little over 5h 26m.

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

    Prices for flights from Key West Airport to Madison Truax Field Airport were last updated today.

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

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

    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 Key West Airport to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents required for your trip to Madison Truax Field Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Madison Truax Field Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Key West to Madison

Compare and see reviews for airlines that fly from Key West to Madison with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $293Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Portage
Fitchburg
Sun Prairie
Cambridge
Oxford
Evansville
Windsor

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Madison. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search for Key West to Madison 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 Key West to Madison right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Madison from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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