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$224+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Apr 12 — Apr 191
Sun 4/12
Sun 4/19
1 adult, Economy
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Cheap 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 March 13, 2026.

This American Airlines deal was found by Cheapflights users on 3/10. 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.
Fri 4/174:20 pm
EYW
-
MSN
1 stop8h 35m
American Airlines
Sat 4/1811:50 am
MSN
-
EYW
2 stops10h 08m
American Airlines
Deal found 3/10$311
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Fri 5/12:29 pm
EYW
-
MSN
1 stop9h 03m
American Airlines
Mon 5/410:19 am
MSN
-
EYW
1 stop6h 57m
American Airlines
Deal found 3/11$329
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/279:49 am
EYW
-
MSN
1 stop24h 19m
Breeze Airways
Tue 3/316:01 pm
MSN
-
EYW
1 stop16h 10m
Breeze Airways
Deal found 3/12$420
This American Airlines deal was found by Cheapflights users on 3/12. 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.
Thu 7/304:40 pm
EYW
-
MSN
1 stop8h 19m
American Airlines
Mon 8/36:30 am
MSN
-
EYW
2 stops8h 38m
American Airlines
Deal found 3/12$439
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Wed 5/66:45 am
EYW
-
MSN
2 stops8h 03m
American Airlines
Sun 5/105:30 am
MSN
-
EYW
2 stops9h 10m
American Airlines
Deal found 3/10$441

Find 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 March 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(American Airlines)

One-way from

$224
(Kiwi.com)
Provider with most accurate pricing for Key West-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Madison Truax Field flights.
Search Deals
From Key West to Madison Truax Field
Search Deals
One-way flight from Key West to Madison Truax Field
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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 March 13, 2026.
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

Cheapest round-trip

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 4/17

3:58 pm-11:55 pm

2 stops8h 57m

Madison Truax Field

Sat 4/18

11:50 am-10:58 pm

2 stops10h 08m

$316

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 5/1

3:58 pm-11:55 pm

2 stops8h 57m

Madison Truax Field

Mon 5/4

9:18 am-6:16 pm

1 stop7h 58m

$334

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 4/16

3:58 pm-11:55 pm

2 stops8h 57m

Madison Truax Field

Fri 4/17

2:18 pm-10:36 pm

2 stops7h 18m

$447
Quickest round-trip

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 4/22

2:35 pm-8:33 pm

1 stop6h 58m

Madison Truax Field

Sat 4/25

5:00 am-11:24 am

1 stop5h 24m

$456

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 4/21

5:25 pm-11:01 pm

1 stop6h 36m

Madison Truax Field

Wed 4/22

5:30 am-12:38 pm

1 stop6h 08m

$498
Cheapest one-way

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 4/15

6:45 am-2:31 pm

2 stops8h 46m

$234
Quickest one-way

Key WestMadison

EYW - MSN

EYWMSN

Key West

Sun 4/19

3:52 pm-9:21 pm

1 stop6h 29m

$570

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 4/15

6:22 pm-10:11 am

3 stops16h 49m

$575

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 4/13

3:52 pm-10:54 pm

1 stop8h 02m

$615

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 4/13

6:45 am-2:31 pm

2 stops8h 46m

$1,168

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Sorted by cheapest first

Compare providers for flights from Key West to Madison

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to Madison in March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Key West-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Madison flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

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.

  • How long is the flight from Key West to Madison?

    A quick flight from Key West to Madison can take about 8h 57m. American Airlines provides one of the quickest options available for as low as $316. Airlines will cover a distance of 1353 mi.

  • 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.

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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