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Key West

$191+ 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 34 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 October 29, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 11/193:37 pmMSN - EYW
1 stop5h 11mAmerican Airlines
Mon 11/246:33 pmEYW - MSN
1 stop5h 57mAmerican Airlines
Deal found 10/29$269
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/610:20 amMSN - EYW
2 stops10h 30mAmerican Airlines
Wed 12/107:00 amEYW - MSN
2 stops9h 23mAmerican Airlines
Deal found 10/27$279
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sat 12/66:08 pmMSN - EYW
1 stop13h 07mBreeze Airways
Fri 12/129:57 amEYW - MSN
1 stop24h 11mBreeze Airways
Deal found 10/27$280
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 12/1011:44 amMSN - EYW
1 stop7h 22mDelta
Sat 12/1312:38 pmEYW - MSN
2 stops9h 20mDelta
Deal found 10/26$309
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/173:35 pmMSN - EYW
1 stop5h 11mAmerican Airlines
Fri 12/264:03 pmEYW - MSN
2 stops8h 56mAmerican Airlines
Deal found 10/29$319
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sat 12/66:08 pmMSN - EYW
2 stops16h 12mMultiple Airlines
Fri 12/129:57 amEYW - MSN
1 stop24h 11mMultiple Airlines
Deal found 10/27$324
This United Airlines deal was found by Cheapflights users on 10/27. 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 10/318:25 amMSN - EYW
1 stop5h 54mUnited Airlines
Sat 11/14:00 pmEYW - MSN
1 stop5h 35mUnited Airlines
Deal found 10/27$336

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$191
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$375
Provider with most accurate pricing for Madison Truax Field-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Key West flights.
Search Deals
From Madison Truax Field to Key West
Search Deals
One-way flight from Madison Truax Field to Key West
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 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

Wed 11/19

3:37 pm-9:48 pm

1 stop5h 11m

Key West

Mon 11/24

6:33 pm-11:30 pm

1 stop5h 57m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

5:38 am-1:48 pm

1 stop7h 10m

Key West

Wed 2/11

7:10 am-3:44 pm

2 stops9h 34m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 2/7

11:29 am-9:47 pm

2 stops9h 18m

Key West

Thu 2/12

2:25 pm-10:51 pm

1 stop9h 26m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 2/6

11:29 am-9:47 pm

2 stops9h 18m

Key West

Wed 2/11

5:21 pm-10:40 pm

1 stop6h 19m

$274

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 1/29

11:15 am-7:42 pm

1 stop7h 27m

Key West

Mon 2/2

6:08 pm-10:37 pm

1 stop5h 29m

$294

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 12/10

11:44 am-8:06 pm

1 stop7h 22m

Key West

Sat 12/13

12:38 pm-8:58 pm

2 stops9h 20m

$309

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 1/29

1:16 pm-9:47 pm

2 stops7h 31m

Key West

Mon 2/2

6:43 pm-11:41 pm

1 stop5h 58m

$309

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 11/22

6:08 pm-8:15 am

1 stop13h 07m

$191

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sun 11/23

12:35 pm-9:35 am

3 stops44h 00m

$278

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sun 11/23

6:00 am-1:46 pm

1 stop6h 46m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 13 results
1
2

Compare providers for flights from Madison to Key West

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 Madison to Key West in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Madison-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Madison-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Key West flights, Cheapflights users trust eDreams the most. eDreams 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 Madison-Key West 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 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 October 24, 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 34 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, November is the cheapest month in which you can book a flight from Madison to Key West (average of $197). Flying from Madison to Key West in June is currently the most expensive (average of $318). 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 October 29, 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
7.9
Good
7,992 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

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
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

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
8,999 reviews
Delta
7.9
Good
7,992 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

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
11,032 reviews
Delta
7.9
Good
7,992 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

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 5h 11m. American Airlines provides one of the quickest options available for as low as $269. 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 ($267), American Airlines ($268), and United Airlines ($348) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 40% 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 Breeze Airways ($191), United Airlines ($295), and American Airlines ($300).

  • 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, November is the cheapest month in which you can book a flight from Madison to Key West (average of $197). Flying from Madison to Key West in June is currently the most expensive (average of $318). 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.

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$488FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$432FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$348Average$498FlexibilityNo cancel feeOn-time69%

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