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$251+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Jul 15 — Jul 221
Wed 7/15
Wed 7/22
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 June 15, 2026.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 7/297:33 pm
EYW
-
MSN
1 stop5h 09m
American Airlines
Fri 8/77:47 am
MSN
-
EYW
1 stop7h 31m
American Airlines
Deal found 6/11$326
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 9/12:20 pm
EYW
-
MSN
2 stops24h 22m
United Airlines
Sat 9/58:10 am
MSN
-
EYW
2 stops28h 19m
United Airlines
Deal found 6/14$926
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Mon 6/292:26 pm
EYW
-
MSN
2 stops9h 46m
United Airlines
Fri 7/36:41 am
MSN
-
EYW
1 stop7h 38m
United Airlines
Deal found 6/14$933
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:20 pm
EYW
-
MSN
2 stops24h 22m
United Airlines
Sat 8/293:55 pm
MSN
-
EYW
2 stops20h 34m
United Airlines
Deal found 6/11$989

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 June 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$326
(American Airlines)
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

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 June 15, 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
Quickest round-trip

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

7:33 pm-11:42 pm

1 stop5h 09m

Madison Truax Field

Fri 8/7

7:47 am-4:18 pm

1 stop7h 31m

$326

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 6/29

2:26 pm-11:12 pm

2 stops9h 46m

Madison Truax Field

Fri 7/3

6:41 am-3:19 pm

1 stop7h 38m

$933

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-8:53 pm

2 stops31h 33m

Madison Truax Field

Sat 9/5

3:55 pm-1:29 pm

2 stops20h 34m

$967

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 8/26

2:20 pm-1:42 pm

2 stops24h 22m

Madison Truax Field

Sat 8/29

3:55 pm-1:29 pm

2 stops20h 34m

$989
Cheapest one-way

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 10/27

1:16 pm-9:53 am

1 stop21h 37m

$251
Quickest one-way

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 10/27

2:30 pm-10:50 pm

2 stops9h 20m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 5h 09m. American Airlines provides one of the quickest options available for as low as $326. Airlines will cover a distance of 1353 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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
Sun Prairie
Middleton
Baraboo
Fitchburg

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