$159+ Cheap flights from Key West to Madison (EYW - MSN)
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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Madison 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 Key West to Madison
Cheapest
Best
Last-minute
One-way
Cheapest flights from Key West to MadisonExplore the most affordable flight options available from Key West to Madison. 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 Key West to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
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.
Thu 11/54:10 pm -
1 stop7h 57m
Sun 11/88:15 am -
1 stop6h 14m
Deal found 10/25![United Airlines logo]()
$574
Best flights from Key West to MadisonDiscover carefully curated flight deals from Key West to Madison 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 Key West to Madison 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 10/27. 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.
Fri 2/511:48 am -
1 stop5h 44m
Sat 2/61:01 pm -
1 stop6h 47m
Deal found 10/27![Delta logo]()
$478
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 2/55:58 pm -
1 stop7h 16m
Sat 2/66:00 am -
1 stop9h 09m
Deal found 10/26![American Airlines logo]()
$483
Last-minute flights from Key West to MadisonDiscover last-minute flight deals from Key West to Madison. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Madison. Data last updated October 30, 2026 and is based on user searches.
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.
Thu 11/54:10 pm -
1 stop7h 57m
Sun 11/88:15 am -
1 stop6h 14m
Deal found 10/25![United Airlines logo]()
$574
One-way flights from Key West to MadisonSearch for one-way flight options from Key West to Madison. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Key West to Madison. 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 10/26. 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.
Mon 1/410:59 am -
1 stop25h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Breeze Airways logo]()
$159
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 11/202:51 pm -
1 stop9h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$394
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.
Mon 1/411:59 am -
2 stops24h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$418
Find flight deals from Key West to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Madison (MSN). 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 | $271 (Kiwi.com) |
One-way from | $159 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to Madison 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 Key West to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Mon 1/4
10:59 am-11:35 am
1 stop25h 36m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Quickest round-trip
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 11/20
2:51 pm-11:37 pm
1 stop9h 46m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$394
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Mon 1/4
11:59 am-11:35 am
2 stops24h 36m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$418
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 2/5
11:48 am-4:32 pm
1 stop5h 44m
Madison Truax Field
Sat 2/6
1:01 pm-8:48 pm
1 stop6h 47m
$478
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 2/5
5:58 pm-12:14 am
1 stop7h 16m
Madison Truax Field
Sat 2/6
6:00 am-4:09 pm
1 stop9h 09m
$483
Sorted by cheapest first
Compare providers for flights from Key West to Madison
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 Key West to Madison in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Key West-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Madison 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 Key West-Madison 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 Key West to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Key West with our price prediction graph.
EYW-MSN
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.
Related info for your journey
Find useful and relevant information for your journey from Key West to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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