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Key West

$288+ Cheap flights from Madison to Key West (MSN - EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
1 adult, Economy
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Cheap 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 July 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/5. 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 9/46:50 pm
MSN
-
EYW
2 stops47h 23m
Breeze Airways
Fri 9/1112:59 pm
EYW
-
MSN
1 stop21h 54m
Breeze Airways
Deal found 7/5$288
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/126:30 am
MSN
-
EYW
1 stop5h 25m
American Airlines
Wed 8/194:50 pm
EYW
-
MSN
1 stop7h 19m
American Airlines
Deal found 7/3$323
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/317:00 am
MSN
-
EYW
1 stop8h 11m
American Airlines
Wed 8/54:50 pm
EYW
-
MSN
1 stop7h 19m
American Airlines
Deal found 7/1$326
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 7/257:55 pm
MSN
-
EYW
1 stop14h 30m
Breeze Airways
Tue 7/281:14 pm
EYW
-
MSN
1 stop21h 33m
Breeze Airways
Deal found 7/1$341
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 7/257:55 pm
MSN
-
EYW
1 stop14h 30m
Breeze Airways
Wed 7/2911:46 am
EYW
-
MSN
2 stops45h 39m
Breeze Airways
Deal found 7/1$345
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/17:55 pm
MSN
-
EYW
1 stop14h 30m
Breeze Airways
Tue 8/41:14 pm
EYW
-
MSN
1 stop21h 33m
Breeze Airways
Deal found 7/2$353
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/179:18 am
MSN
-
EYW
1 stop5h 32m
American Airlines
Wed 7/227:33 pm
EYW
-
MSN
1 stop5h 09m
American Airlines
Deal found 7/1$364
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 10/138:25 am
MSN
-
EYW
1 stop6h 46m
American Airlines
Sat 10/177:19 pm
EYW
-
MSN
1 stop5h 38m
American Airlines
Deal found 7/1$379
This American Airlines deal was found by Cheapflights users on 7/4. 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 8/289:48 am
MSN
-
EYW
1 stop5h 30m
American Airlines
Mon 8/314:50 pm
EYW
-
MSN
1 stop7h 19m
American Airlines
Deal found 7/4$389
This United Airlines deal was found by Cheapflights users on 7/5. 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.
Thu 7/308:10 am
MSN
-
EYW
1 stop6h 09m
United Airlines
Tue 8/44:00 pm
EYW
-
MSN
1 stop8h 12m
United Airlines
Deal found 7/5$404
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 11/126:30 am
MSN
-
EYW
1 stop7h 46m
United Airlines
Tue 11/172:55 pm
EYW
-
MSN
1 stop9h 42m
United Airlines
Deal found 7/2$418

Find 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 July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$288
(Kiwi.com)

Popular in

June

Cheapest in

July

Average price

$328
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
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 6, 2026.
Use the filters below to find and compare flights from Madison to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 10/13

8:25 am-4:11 pm

1 stop6h 46m

Key West

Sat 10/17

7:19 pm-11:57 pm

1 stop5h 38m

$379

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 11/12

6:30 am-3:16 pm

1 stop7h 46m

Key West

Tue 11/17

2:55 pm-11:37 pm

1 stop9h 42m

$418

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 10/27

8:25 am-4:11 pm

1 stop6h 46m

Key West

Sat 11/7

8:06 am-2:55 pm

2 stops7h 49m

$445

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 10/24

7:15 am-4:58 pm

2 stops8h 43m

Key West

Fri 10/30

7:19 pm-11:57 pm

1 stop5h 38m

$448

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 10/24

6:00 am-7:51 pm

2 stops12h 51m

Key West

Sat 10/31

6:11 pm-10:53 pm

1 stop5h 42m

$465

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/17

8:10 am-3:19 pm

1 stop6h 09m

Key West

Wed 7/22

2:26 pm-11:12 pm

2 stops9h 46m

$473

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 9/4

11:22 am-7:57 pm

1 stop7h 35m

Key West

Fri 9/11

6:19 pm-10:53 pm

1 stop5h 34m

$488

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 11/28

11:11 am-7:43 pm

1 stop7h 32m

Key West

Sat 12/26

2:30 pm-9:38 pm

1 stop8h 08m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Sorted by cheapest first

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub the most. FlightHub 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?

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 61 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, July 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 June is currently the most expensive (average of $578). 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 July 6, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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
7.8
Good
8,453 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.8

Overall

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.8
Good
8,453 reviews
Delta
7.8
Good
8,453 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.8

Overall

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
United Airlines
7.4
Good
9,938 reviews
Delta
7.8
Good
8,453 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.8

Overall

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,784 reviews
Delta
7.8
Good
8,453 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.8

Overall

7.8

Boarding

8.1

Food

7.2

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

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 46m. United Airlines provides one of the quickest options available for as low as $445. 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, American Airlines ($282), Delta ($302), and United Airlines ($313) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 34% less than the average price by searching for these airlines.

  • 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, July 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 June is currently the most expensive (average of $578). 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 July 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$282Average$444FlexibilityNo cancel feeOn-time71%
DeltaCheapest$302Average$457FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$313Average$417FlexibilityNo cancel feeOn-time69%

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