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Key West

$219+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June, 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 June 12, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$219
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$373
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. 10% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

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 11/196:38 amMSN - EYW
1 stop8h 38mAmerican Airlines
Mon 11/245:26 pmEYW - MSN
1 stop4h 58mAmerican Airlines
Deal found 6/11$269
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1510:50 amMSN - EYW
1 stop5h 42mDelta
Tue 7/226:27 pmEYW - MSN
1 stop5h 07mDelta
Deal found 6/10$294
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/218:20 amMSN - EYW
2 stops22h 40mUnited Airlines
Mon 6/306:45 pmEYW - MSN
2 stops20h 09mUnited Airlines
Deal found 6/10$407

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 June 12, 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

6:38 am-4:16 pm

1 stop8h 38m

Key West

Mon 11/24

5:26 pm-9:24 pm

1 stop4h 58m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 7/15

10:50 am-5:32 pm

1 stop5h 42m

Key West

Tue 7/22

6:27 pm-10:34 pm

1 stop5h 07m

$294

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/9

6:40 am-12:15 pm

2 stops28h 35m

Key West

Sat 8/16

8:45 am-10:30 pm

2 stops14h 45m

$410

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 11/19

9:48 am-10:31 am

2 stops47h 43m

Key West

Mon 11/24

11:11 am-9:08 am

3 stops46h 57m

$1,113

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 7/23

6:27 am-1:51 pm

1 stop6h 24m

$219

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 7/24

10:50 am-5:32 pm

1 stop5h 42m

$320

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 7/23

10:19 am-11:41 am

3 stops24h 22m

$338

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 7/24

3:50 pm-2:00 pm

3 stops45h 10m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 9, 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 41 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 June 12, 2025.
Read reviews from past customers who have flown Breeze Airways, Delta and United 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.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,950 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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), Delta ($294), and United Airlines ($410) 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 American Airlines ($219), Delta ($320), and United Airlines ($602).

  • 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$598FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$263Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%

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