$187+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
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 October 30, 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 October 30, 2026.
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:30 am -
1 stop6h 41m
Tue 1/125:00 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 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
Mon 11/1610:59 am -
1 stop23h 51m
Deal found 10/28![Breeze Airways logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:00 am -
1 stop7h 23m
Sun 12/204:04 pm -
1 stop6h 36m
Deal found 10/28![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/285:01 am -
1 stop5h 45m
Sat 12/55:01 pm -
1 stop6h 35m
Deal found 10/28![American Airlines logo]()
$449
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/305:00 am -
1 stop5h 41m
Wed 1/63:15 pm -
1 stop7h 23m
Deal found 10/26![United Airlines logo]()
$453
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:24 pm -
1 stop5h 23m
Tue 11/176:35 pm -
1 stop6h 08m
Deal found 10/26![American Airlines logo]()
$454
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:10 pm -
1 stop15h 09m
Mon 1/410:59 am -
1 stop25h 36m
Deal found 10/26![Breeze Airways logo]()
$470
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:10 pm -
2 stops40h 09m
Tue 12/81:16 pm -
1 stop21h 42m
Deal found 10/29![Multiple Airlines logo]()
$476
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:30 am -
1 stop6h 29m
Wed 12/96:06 pm -
1 stop5h 46m
Deal found 10/29![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:51 am -
1 stop7h 29m
Sat 11/77:40 am -
1 stop5h 51m
Deal found 10/28![Delta logo]()
$479
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 12/136:52 am -
1 stop8h 15m
Tue 1/124:16 pm -
2 stops8h 58m
Deal found 10/28![American Airlines logo]()
$488
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 October 30, 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 October 30, 2026.
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:30 am -
1 stop6h 41m
Tue 1/125:00 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:00 am -
1 stop7h 23m
Sun 12/204:04 pm -
1 stop6h 36m
Deal found 10/28![United Airlines logo]()
$394
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.
Mon 3/18:10 am -
1 stop6h 31m
Mon 3/86:32 pm -
1 stop5h 36m
Deal found 10/29![American Airlines logo]()
$394
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/305:00 am -
1 stop5h 41m
Wed 1/63:15 pm -
1 stop7h 23m
Deal found 10/26![United Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sun 12/136:52 am -
1 stop8h 15m
Tue 1/124:16 pm -
2 stops8h 58m
Deal found 10/25![American Airlines logo]()
$488
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 2/207:01 am -
2 stops11h 31m
Wed 2/246:15 pm -
1 stop6h 57m
Deal found 10/27![American Airlines logo]()
$488
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:25 am -
1 stop8h 04m
Thu 12/1012:05 pm -
1 stop6h 32m
Deal found 10/29![United Airlines logo]()
$539
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 3/117:01 am -
1 stop5h 36m
Tue 3/236:32 pm -
1 stop5h 36m
Deal found 10/28![American Airlines logo]()
$496
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:00 am -
1 stop5h 41m
Tue 1/53:15 pm -
1 stop7h 23m
Deal found 10/26![United Airlines logo]()
$548
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:05 am -
1 stop7h 08m
Wed 2/33:15 pm -
1 stop7h 23m
Deal found 10/29![United Airlines logo]()
$588
Last-minute flights from Madison to Key WestDiscover last-minute flight deals from Madison to Key West. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Key West. Data last updated October 30, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:51 am -
1 stop7h 29m
Sat 11/77:40 am -
1 stop5h 51m
Deal found 10/28![Delta logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 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
Mon 11/1610:59 am -
1 stop23h 51m
Deal found 10/28![Breeze Airways logo]()
$391
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:24 pm -
1 stop5h 23m
Tue 11/176:35 pm -
1 stop6h 08m
Deal found 10/26![American Airlines logo]()
$454
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:10 pm -
2 stops40h 09m
Tue 12/81:16 pm -
1 stop21h 42m
Deal found 10/29![Multiple Airlines logo]()
$476
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:30 am -
1 stop6h 29m
Fri 12/46:06 pm -
1 stop5h 46m
Deal found 10/29![Delta logo]()
$478
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:10 pm -
2 stops40h 09m
Mon 12/710:59 am -
1 stop23h 51m
Deal found 10/29![Multiple Airlines logo]()
$514
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:10 am -
1 stop6h 42m
Thu 12/1012:05 pm -
1 stop6h 32m
Deal found 10/29![United Airlines logo]()
$499
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:30 am -
2 stops12h 30m
Fri 12/46:06 pm -
1 stop5h 46m
Deal found 10/29![Delta logo]()
$518
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/285:01 am -
1 stop5h 45m
Sat 12/55:01 pm -
1 stop6h 35m
Deal found 10/28![American Airlines logo]()
$449
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:15 am -
1 stop6h 14m
Fri 12/44:10 pm -
1 stop7h 13m
Deal found 10/29![United Airlines logo]()
$504
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/293:40 pm -
1 stop17h 39m
Fri 12/412:59 pm -
1 stop21h 59m
Deal found 10/29![Breeze Airways logo]()
$501
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 October 30, 2026.
Search for one-way flight options from Madison to Key West. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/3110:31 am -
1 stop26h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$187
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:10 pm -
1 stop15h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Breeze Airways logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/276:10 am -
1 stop6h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![United Airlines logo]()
$334
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 3/318:10 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/25. 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 11/277:05 am -
2 stops8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/30. 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 3/316:45 am -
2 stops9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/272:40 pm -
3 stops20h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$411
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:06 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$431
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $304 (Kiwi.com) |
One-way from | $187 (Kiwi.com) |
Popular in | September |
Cheapest in | October |
Average price | $385 |
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 October 30, 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
Wed 3/31
10:31 am-2:26 pm
1 stop26h 55m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Thu 12/24
6:10 pm-10:19 am
1 stop15h 09m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$311
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Fri 11/27
6:10 am-1:52 pm
1 stop6h 42m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$334
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 3/31
8:10 am-3:41 pm
1 stop6h 31m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$339
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Sun 12/13
5:30 am-1:11 pm
1 stop6h 41m
Key West
Tue 1/12
5:00 pm-10:44 pm
1 stop6h 44m
$359
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Fri 11/27
7:05 am-4:23 pm
2 stops8h 18m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$385
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Thu 12/17
7:00 am-3:23 pm
1 stop7h 23m
Key West
Sun 12/20
4:04 pm-9:40 pm
1 stop6h 36m
$394
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Mon 3/1
8:10 am-3:41 pm
1 stop6h 31m
Key West
Mon 3/8
6:32 pm-11:08 pm
1 stop5h 36m
$394
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 3/31
6:45 am-5:02 pm
2 stops9h 17m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$399
Quickest round-trip
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 12/23
5:06 am-11:51 am
1 stop5h 45m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$431
Showing 1-10 of 17 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 71 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, October is the cheapest month in which you can book a flight from Madison to Key West (average of $385). 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 $490 and $614 in February.The cheapest round-trip price found within the last 5 days was $304 on Breeze Airways (Feb 7-Feb 12).
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 30, 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.
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Comfort
7.8
Food
7.2
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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Top 3 airlines flying from Madison to Key West
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$445 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$302 | Average$457 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$313 | Average$438 | FlexibilityNo cancel fee | On-time69% |