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$258+ Cheap flights from Key West to Madison (EYW - MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
août 4 — août 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheap flight deals from Key West to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated juillet 30, 2025.

Round-trip from

$269
(Delta)

One-way from

$258
(Booking.com)
From Key West to Madison Truax Field
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One-way flight from Key West to Madison Truax Field
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Find flight deals from Key West to Madison

Cheapest flights from Key West to Madison
Explore the most affordable flight options available from Key West to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juillet 30, 2025.

This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 8/206:22 pmEYW - MSN
1 stop5h 26mDelta
lun. 9/15:40 amMSN - EYW
1 stop6h 25mDelta
Deal found 7/30$269
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/214:49 pmEYW - MSN
1 stop8h 10mAmerican Airlines
lun. 8/256:46 amMSN - EYW
1 stop8h 36mAmerican Airlines
Deal found 7/29$294
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/213:41 pmEYW - MSN
3 stops24h 21mUnited Airlines
lun. 8/256:30 amMSN - EYW
2 stops30h 55mUnited Airlines
Deal found 7/29$948

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated juillet 30, 2025.
Use the filters below to find and compare flights from Key West to Madison that are best for you.

Fly from

Key West

Fly to

Madison

Route

Depart

Return

Price

Key WestMadison

EYW - MSN

EYWMSN

Key West

mer. 8/20

6:22 pm-10:48 pm

1 stop5h 26m

Madison Truax Field

lun. 9/1

5:40 am-1:05 pm

1 stop6h 25m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

jeu. 8/21

4:49 pm-11:59 pm

1 stop8h 10m

Madison Truax Field

lun. 8/25

6:46 am-4:22 pm

1 stop8h 36m

$294

Key WestMadison

EYW - MSN

EYWMSN

Key West

jeu. 8/21

3:41 pm-3:02 pm

3 stops24h 21m

Madison Truax Field

lun. 8/25

6:30 am-2:25 pm

2 stops30h 55m

$948

Key WestMadison

EYW - MSN

EYWMSN

Key West

ven. 8/15

1:47 pm-8:01 am

1 stop19h 14m

$258

Key WestMadison

EYW - MSN

EYWMSN

Key West

ven. 8/15

2:12 pm-10:15 pm

2 stops9h 03m

$284

Key WestMadison

EYW - MSN

EYWMSN

Key West

ven. 8/15

10:23 am-9:39 am

2 stops24h 16m

$345

Key WestMadison

EYW - MSN

EYWMSN

Key West

sam. 8/16

3:59 pm-11:27 pm

1 stop8h 28m

$528

Key WestMadison

EYW - MSN

EYWMSN

Key West

ven. 8/15

12:10 pm-8:58 pm

3 stops33h 48m

$1,256

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Key West to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Key West with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated juillet 30, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Breeze Airways from Key West to Madison by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Breeze Airways
8.0
Very good
191 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Key West to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Key West to Madison round-trip?

    Cheapflights users have booked flights from Key West to Madison round-trip from $269. Other airlines that can offer you cheap pricing are American Airlines, from $294, and United Airlines, from $948.

  • What are the cheapest airlines to fly from Key West to Madison one-way?

    One-way options have recently been found by users for as low as $258 on Breeze Airways. Other airlines that offer cheap prices include United Airlines from $284 and American Airlines from $528 one-way.

  • Can I find deals for flights from Key West to Madison that include hotel bookings?

    Yes. In addition to deals on Key West to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Madison.

  • Can I find deals for business class flights from Key West to Madison?

    Yes. Cheapflights offers flight deals from Key West to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Key West to Madison?

    Currently, January is the cheapest month in which you can book a flight from Key West to Madison (average of $338). Flying from Key West to Madison in March is currently the most expensive (average of $422). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top airline flying from Key West to Madison

Discover the top airline that operate flights from Key West to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated juillet 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$293Average$418FlexibilityNo cancel feeOn-time71%

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