$280+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Key West
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Cheapest flights from Madison to Key WestExplore 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 16, 2026.
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 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/16:00 pm -
1 stop13h 44m
Fri 11/612:59 pm -
1 stop21h 59m
Deal found 9/14![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/16:00 pm -
1 stop13h 44m
Thu 11/510:59 am -
1 stop7h 21m
Deal found 9/14![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 11/410:38 am -
1 stop20h 26m
Fri 11/612:59 pm -
1 stop21h 59m
Deal found 9/14![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/16:00 pm -
1 stop13h 44m
Tue 11/101:16 pm -
1 stop21h 42m
Deal found 9/14![Multiple Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 9/14. 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 11/31:37 pm -
1 stop5h 24m
Wed 11/116:05 pm -
1 stop5h 45m
Deal found 9/14![Delta logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/56:00 pm -
1 stop12h 35m
Fri 11/62:58 pm -
1 stop20h 00m
Deal found 9/14![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/126:00 pm -
1 stop15h 19m
Tue 11/171:16 pm -
1 stop21h 42m
Deal found 9/14![Breeze Airways logo]()
$364
This Delta deal was found by Cheapflights users on 9/15. 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 10/1311:14 am -
1 stop7h 47m
Tue 10/206:10 pm -
1 stop5h 53m
Deal found 9/15![Delta logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/16:00 pm -
1 stop13h 44m
Mon 11/99:20 am -
1 stop25h 30m
Deal found 9/14![Multiple Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Sun 9/276:00 pm -
1 stop15h 19m
Thu 10/110:59 am -
1 stop7h 21m
Deal found 9/12![Breeze Airways logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Thu 12/106:10 pm -
1 stop15h 09m
Mon 12/1410:59 am -
1 stop23h 51m
Deal found 9/12![Breeze Airways logo]()
$385
Best flights from Madison to Key WestDiscover carefully curated flight deals from Madison to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Madison to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 1/2811:11 am -
1 stop7h 32m
Wed 2/32:30 pm -
1 stop6h 41m
Deal found 9/15![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 3/35:10 am -
2 stops10h 52m
Wed 3/104:00 pm -
1 stop8h 03m
Deal found 9/13![United Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 9/15. 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 3/16:16 am -
1 stop5h 31m
Mon 3/84:40 pm -
1 stop8h 04m
Deal found 9/15![American Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 9/13. 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 10/1311:14 am -
1 stop7h 47m
Sat 10/176:11 pm -
1 stop5h 51m
Deal found 9/13![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 1/255:45 am -
1 stop6h 23m
Wed 2/32:30 pm -
1 stop6h 41m
Deal found 9/15![Delta logo]()
$436
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 9/267:17 am -
2 stops11h 00m
Wed 9/302:15 pm -
1 stop7h 35m
Deal found 9/11![American Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 9/15. 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 1/1311:11 am -
1 stop7h 32m
Sat 1/167:00 am -
1 stop7h 20m
Deal found 9/15![Delta logo]()
$479
This American Airlines deal was found by Cheapflights users on 9/16. 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 2/207:00 am -
1 stop7h 56m
Sat 2/272:25 pm -
1 stop9h 26m
Deal found 9/16![American Airlines logo]()
$553
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:45 pm -
1 stop5h 15m
Wed 9/306:19 pm -
1 stop5h 22m
Deal found 9/11![Delta logo]()
$505
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/135:00 am -
2 stops10h 11m
Sat 10/177:19 pm -
1 stop5h 38m
Deal found 9/12![American Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 1/2811:11 am -
1 stop7h 32m
Thu 2/47:00 am -
2 stops16h 55m
Deal found 9/15![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 1/2411:11 am -
1 stop5h 00m
Sat 1/307:00 am -
1 stop5h 35m
Deal found 9/15![Delta logo]()
$518
Last-minute flights from Madison to Key WestDiscover last-minute flight deals from Madison to Key West. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Key West. Data last updated September 16, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 9/255:50 am -
1 stop6h 03m
Tue 10/206:10 pm -
1 stop5h 53m
Deal found 9/15![Delta logo]()
$440
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:45 pm -
1 stop5h 15m
Wed 9/306:19 pm -
1 stop5h 22m
Deal found 9/11![Delta logo]()
$505
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 9/267:17 am -
2 stops11h 00m
Wed 9/302:15 pm -
1 stop7h 35m
Deal found 9/11![American Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Sun 9/276:00 pm -
1 stop15h 19m
Thu 10/110:59 am -
1 stop7h 21m
Deal found 9/12![Breeze Airways logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Wed 9/3010:33 am -
1 stop23h 48m
Sun 10/410:59 am -
1 stop7h 21m
Deal found 9/12![Breeze Airways logo]()
$501
This Delta deal was found by Cheapflights users on 9/15. 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 10/1311:14 am -
1 stop7h 47m
Tue 10/206:10 pm -
1 stop5h 53m
Deal found 9/15![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 9/15. 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 10/1311:14 am -
1 stop7h 47m
Sat 10/176:11 pm -
1 stop5h 51m
Deal found 9/15![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 9/12. 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 -
1 stop6h 46m
Sat 10/177:19 pm -
1 stop5h 38m
Deal found 9/12![American Airlines logo]()
$439
This American Airlines deal was found by Cheapflights users on 9/15. 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 -
1 stop6h 46m
Tue 10/203:06 pm -
2 stops9h 19m
Deal found 9/15![American Airlines logo]()
$487
One-way flights from Madison to Key WestSearch for one-way flight options from Madison to Key West. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Madison to Key West. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/256:00 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 1/118:22 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$569
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 1/1111:00 am -
2 stops7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$735
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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (Kiwi.com) |
Popular in | September |
Cheapest in | August |
Average price | $646 |
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 7,457,451 searches. Data last updated September 16, 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
Cheapest round-trip
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Thu 1/28
11:11 am-7:43 pm
1 stop7h 32m
Key West
Wed 2/3
2:30 pm-8:11 pm
1 stop6h 41m
$365
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 3/3
5:10 am-5:02 pm
2 stops10h 52m
Key West
Wed 3/10
4:00 pm-11:03 pm
1 stop8h 03m
$373
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Mon 3/1
6:16 am-12:47 pm
1 stop5h 31m
Key West
Mon 3/8
4:40 pm-11:44 pm
1 stop8h 04m
$430
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Tue 10/13
11:14 am-8:01 pm
1 stop7h 47m
Key West
Sat 10/17
6:11 pm-11:02 pm
1 stop5h 51m
$436
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Mon 1/25
5:45 am-1:08 pm
1 stop6h 23m
Key West
Wed 2/3
2:30 pm-8:11 pm
1 stop6h 41m
$436
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Fri 9/25
6:00 am-5:55 pm
2 stops10h 55m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$475
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 1/13
11:11 am-7:43 pm
1 stop7h 32m
Key West
Sat 1/16
7:00 am-1:20 pm
1 stop7h 20m
$479
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Sat 9/26
1:45 pm-8:00 pm
1 stop5h 15m
Key West
Wed 9/30
6:19 pm-10:41 pm
1 stop5h 22m
$505
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Thu 1/28
11:11 am-7:43 pm
1 stop7h 32m
Key West
Thu 2/4
7:00 am-10:55 pm
2 stops16h 55m
$517
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Sun 1/24
11:11 am-5:11 pm
1 stop5h 00m
Key West
Sat 1/30
7:00 am-11:35 am
1 stop5h 35m
$518
Showing 1-10 of 15 resultsSorted 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MSN-EYW
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, August is the cheapest month in which you can book a flight from Madison to Key West (average of $388). Flying from Madison to Key West in September is currently the most expensive (average of $646). 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.
How much does it cost to fly round-trip from Madison to Key West?
Airfare is below average for this route at the moment.
Madison to Key West flights typically cost between $408 and $680 in November.The cheapest round-trip price found within the last 5 days was $280 on Multiple Airlines (Nov 1-Nov 6).
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 16, 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.
Boarding
8.1
Overall
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Overall
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Overall
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Overall
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Madison to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 16, 2026.
Madison and Key West flights
Browse other Madison and Key West flight options. Last updated on September 16, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on September 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$282 | Average$448 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$302 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$313 | Average$438 | FlexibilityNo cancel fee | On-time69% |