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$114+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
may. 5 — may. 121
lun. 5/5
lun. 5/12
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 September, booked 77 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 abril 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$114
(Delta)

Popular in

March

Cheapest in

August

Average price

$405
Provider with most accurate pricing for Madison Truax Field-Key West flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Key West flights.
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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. 14% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 30, 2025.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
jue. 5/296:45 amMSN - EYW
1 stop8h 55mAmerican Airlines
mar. 6/35:24 pmEYW - MSN
1 stop7h 21mAmerican Airlines
Deal found 4/28$269
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/42:54 pmMSN - EYW
2 stops26h 11mUnited Airlines
mar. 7/88:45 amEYW - MSN
2 stops30h 09mUnited Airlines
Deal found 4/29$435
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/45:45 amMSN - EYW
1 stop4h 45mDelta
dom. 5/116:25 pmEYW - MSN
1 stop5h 36mDelta
Deal found 4/27$509

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 abril 30, 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

jue. 5/29

6:45 am-4:40 pm

1 stop8h 55m

Key West

mar. 6/3

5:24 pm-11:45 pm

1 stop7h 21m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

vie. 7/4

2:54 pm-6:05 pm

2 stops26h 11m

Key West

mar. 7/8

8:45 am-1:54 pm

2 stops30h 09m

$435

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

dom. 5/4

5:45 am-11:30 am

1 stop4h 45m

Key West

dom. 5/11

6:25 pm-11:01 pm

1 stop5h 36m

$509

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

vie. 5/30

7:00 am-8:07 pm

2 stops12h 07m

$114

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

vie. 5/30

6:45 am-4:40 pm

1 stop8h 55m

$250

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

lun. 6/2

2:35 pm-8:00 am

3 stops16h 25m

$568

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Key West flight deals on Cheapflights vs. FlightHub >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 April 25, 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 75 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 $493). 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.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 abril 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Madison to Key West. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,929 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

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
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

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
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

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
7,929 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

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.

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

    According to our current data, American Airlines ($269), United Airlines ($419), and Delta ($438) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 38% 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 ($114), American Airlines ($250), and United Airlines ($568).

  • 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 $493). 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 abril 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$597FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

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