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$229+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$294
(Delta)

One-way from

$229
(United Airlines)
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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/33:12 pmEYW - MSN
1 stop8h 21mUnited Airlines
Mon 10/66:17 amMSN - EYW
1 stop7h 12mUnited Airlines
Deal found 9/14$294
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:00 amEYW - MSN
2 stops10h 09mDelta
Mon 10/65:30 amMSN - EYW
1 stop4h 57mDelta
Deal found 9/14$299
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:25 amEYW - MSN
2 stops12h 45mAmerican Airlines
Mon 10/67:40 amMSN - EYW
2 stops10h 42mAmerican Airlines
Deal found 9/14$304
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:10 pmEYW - MSN
1 stop5h 48mDelta
Sun 10/55:40 amMSN - EYW
1 stop6h 22mDelta
Deal found 9/14$344
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:49 pmEYW - MSN
1 stop8h 30mAmerican Airlines
Mon 9/297:30 amMSN - EYW
1 stop6h 44mAmerican Airlines
Deal found 9/14$349
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:10 pmEYW - MSN
1 stop5h 48mDelta
Tue 10/75:30 amMSN - EYW
1 stop4h 57mDelta
Deal found 9/14$369
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/109:57 amEYW - MSN
1 stop24h 11mMultiple Airlines
Mon 10/137:59 pmMSN - EYW
2 stops14h 06mMultiple Airlines
Deal found 9/14$484
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:17 pmEYW - MSN
1 stop5h 53mAmerican Airlines
Mon 10/66:00 amMSN - EYW
1 stop5h 58mAmerican Airlines
Deal found 9/14$498
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:17 pmEYW - MSN
1 stop5h 53mAmerican Airlines
Sun 10/56:20 amMSN - EYW
1 stop6h 40mAmerican Airlines
Deal found 9/14$523
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:47 pmEYW - MSN
2 stops7h 04mAmerican Airlines
Mon 10/136:45 amMSN - EYW
2 stops11h 37mAmerican Airlines
Deal found 9/14$573

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 September 15, 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

Fri 10/3

6:10 pm-10:58 pm

1 stop5h 48m

Madison Truax Field

Mon 10/6

5:30 am-1:02 pm

1 stop6h 32m

$294

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/3

3:12 pm-10:33 pm

1 stop8h 21m

Madison Truax Field

Mon 10/6

6:17 am-2:29 pm

1 stop7h 12m

$294

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 10/2

6:10 pm-10:58 pm

1 stop5h 48m

Madison Truax Field

Mon 10/6

5:30 am-11:27 am

1 stop4h 57m

$294

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/3

11:25 am-11:10 pm

2 stops12h 45m

Madison Truax Field

Mon 10/6

7:40 am-7:22 pm

2 stops10h 42m

$304

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/3

6:10 pm-10:58 pm

1 stop5h 48m

Madison Truax Field

Sun 10/5

5:40 am-1:02 pm

1 stop6h 22m

$344

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/20

1:30 pm-8:15 pm

1 stop7h 45m

Madison Truax Field

Tue 2/24

11:11 am-7:44 pm

1 stop7h 33m

$344

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 10/2

6:10 pm-10:58 pm

1 stop5h 48m

Madison Truax Field

Sun 10/5

5:40 am-1:02 pm

1 stop6h 22m

$344

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 9/25

4:49 pm-12:19 am

1 stop8h 30m

Madison Truax Field

Mon 9/29

7:30 am-3:14 pm

1 stop6h 44m

$349

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/20

6:31 am-4:36 pm

2 stops11h 05m

Madison Truax Field

Tue 2/24

6:16 am-3:23 pm

1 stop8h 07m

$354

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 2/4

4:15 pm-9:05 pm

1 stop5h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 15 results
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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 48m. Delta provides one of the quickest options available for as low as $294. 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.

  • 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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