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Key West

$229+ Cheap flights from Madison to Key West (MSN - EYW)

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Key West are usually found in August or October, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Madison to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Key West (EYW). 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 11, 2025.

Round-trip from

$264
(United Airlines)

One-way from

$229
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$378
From Madison Truax Field to Key West
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One-way flight from Madison Truax Field to Key West
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Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Madison to Key West

Cheapest flights from Madison to Key West
Explore the most affordable flight options available from Madison to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/256:45 amMSN - EYW
1 stop8h 33mAmerican Airlines
Wed 10/291:38 pmEYW - MSN
1 stop8h 40mAmerican Airlines
Deal found 9/10$269
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 10/255:30 amMSN - EYW
1 stop6h 32mDelta
Wed 10/297:40 amEYW - MSN
2 stops9h 56mDelta
Deal found 9/9$274
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 9/277:30 amMSN - EYW
2 stops10h 29mAmerican Airlines
Wed 10/12:30 pmEYW - MSN
1 stop7h 36mAmerican Airlines
Deal found 9/11$324
This American Airlines deal was found by Cheapflights users on 9/11. 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 12/53:35 pmMSN - EYW
1 stop5h 43mAmerican Airlines
Sat 12/138:00 amEYW - MSN
1 stop7h 47mAmerican Airlines
Deal found 9/11$342
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 10/66:20 amMSN - EYW
2 stops9h 56mAmerican Airlines
Tue 10/144:37 pmEYW - MSN
1 stop7h 19mAmerican Airlines
Deal found 9/11$346
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 9/131:20 pmMSN - EYW
1 stop5h 47mDelta
Sat 9/206:10 pmEYW - MSN
1 stop5h 48mDelta
Deal found 9/9$349
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 11/1012:20 pmMSN - EYW
1 stop8h 28mAmerican Airlines
Fri 11/141:23 pmEYW - MSN
1 stop7h 19mAmerican Airlines
Deal found 9/9$369

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Key West 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 11, 2025.
Use the filters below to find and compare flights from Madison to Key West that are best for you.

Fly from

Madison

Fly to

Key West

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 1/5

5:00 am-12:20 pm

1 stop6h 20m

Key West

Wed 1/14

4:15 pm-9:05 pm

1 stop5h 50m

$264

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 10/25

5:30 am-1:02 pm

1 stop6h 32m

Key West

Wed 10/29

7:40 am-4:36 pm

2 stops9h 56m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 9/27

7:30 am-6:59 pm

2 stops10h 29m

Key West

Wed 10/1

2:30 pm-9:06 pm

1 stop7h 36m

$324

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 12/24

5:00 am-12:20 pm

1 stop6h 20m

Key West

Wed 12/31

12:22 pm-7:05 pm

1 stop7h 43m

$344

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 2/4

8:15 am-3:17 pm

1 stop6h 02m

Key West

Sat 2/7

4:15 pm-9:05 pm

1 stop5h 50m

$349

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 1/30

8:15 am-3:17 pm

1 stop6h 02m

Key West

Thu 2/5

4:15 pm-9:05 pm

1 stop5h 50m

$349

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 1/31

8:15 am-3:17 pm

1 stop6h 02m

Key West

Sat 2/7

4:15 pm-9:05 pm

1 stop5h 50m

$349

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 2/3

6:30 am-3:17 pm

1 stop7h 47m

Key West

Wed 2/11

4:15 pm-9:05 pm

1 stop5h 50m

$349

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

8:15 am-3:17 pm

1 stop6h 02m

Key West

Sat 2/7

4:15 pm-9:05 pm

1 stop5h 50m

$349

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 10/17

11:27 am-8:06 pm

1 stop7h 39m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 14 results
1
2

Best time to book a flight from Madison to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Madison 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.

Cheapflights Insights

Everything you need to know about your flight from Madison to Key West

How far ahead should I book a flight from Madison to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Key West. Price data was last updated on August 29, 2025.

The price you pay for your flight from Madison to Key West may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Madison to Key West (average of $328). Flying from Madison to Key West in March is currently the most expensive (average of $491). 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.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Madison to Key West to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Madison to Key West. 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 Madison to Key West?

    A quick flight from Madison to Key West can take about 6h 20m. United Airlines provides one of the quickest options available for as low as $264. Madison and Key West are separated by a distance of 1353 mi. This flight may include one or multiple stops.

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

    According to our current data, Delta ($238), American Airlines ($268), and United Airlines ($288) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 46% less than the average price by searching for these airlines.

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

    The cheapest airlines for a one-way flight from Madison to Key West are Delta ($229), American Airlines ($229), and United Airlines ($229).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Key West 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 Madison to Key West?

    Currently, August is the cheapest month in which you can book a flight from Madison to Key West (average of $328). Flying from Madison to Key West in March is currently the most expensive (average of $491). 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

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Top 3 airlines flying from Madison to Key West

Discover the top 3 airlines that operate flights from Madison to Key West. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$488FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$411FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

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