$197+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Oct 17 — Oct 241
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
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Best
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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 September 17, 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 September 17, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:10 pm -
1 stop6h 00m
Sat 12/55:00 am -
1 stop5h 24m
Deal found 9/14![United Airlines logo]()
$356
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 11/135:07 pm -
1 stop8h 06m
Mon 11/168:05 am -
1 stop6h 01m
Deal found 9/15![American Airlines logo]()
$377
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.
Fri 12/411:43 am -
1 stop5h 47m
Sat 12/51:32 pm -
1 stop5h 30m
Deal found 9/14![Delta logo]()
$396
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:14 pm -
1 stop7h 53m
Sat 12/55:00 am -
2 stops9h 26m
Deal found 9/14![American Airlines logo]()
$487
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:42 am -
1 stop5h 38m
Mon 10/55:50 am -
1 stop6h 03m
Deal found 9/16![Delta logo]()
$579
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.
Wed 12/1612:05 pm -
1 stop6h 32m
Thu 12/175:00 am -
1 stop5h 41m
Deal found 9/15![United Airlines logo]()
$677
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.
Tue 12/14:53 pm -
1 stop8h 06m
Wed 12/28:05 am -
1 stop6h 01m
Deal found 9/16![American Airlines logo]()
$713
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.
Thu 10/12:15 pm -
1 stop7h 35m
Mon 10/57:14 am -
2 stops8h 44m
Deal found 9/16![American Airlines logo]()
$735
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 September 17, 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 September 17, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:10 pm -
1 stop6h 00m
Sat 12/55:00 am -
1 stop5h 24m
Deal found 9/14![United Airlines logo]()
$356
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:07 pm -
1 stop7h 36m
Mon 11/165:00 am -
1 stop5h 54m
Deal found 9/13![American Airlines logo]()
$377
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.
Fri 12/411:43 am -
1 stop5h 47m
Sat 12/51:32 pm -
1 stop5h 30m
Deal found 9/14![Delta logo]()
$396
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:42 am -
1 stop5h 38m
Mon 10/55:50 am -
1 stop6h 03m
Deal found 9/16![Delta logo]()
$579
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.
Tue 12/14:53 pm -
1 stop8h 06m
Wed 12/28:05 am -
1 stop6h 01m
Deal found 9/16![American Airlines logo]()
$713
Last-minute flights from Key West to MadisonDiscover last-minute flight deals from Key West to Madison. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Madison. Data last updated September 17, 2026 and is based on user searches.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:42 am -
1 stop5h 38m
Mon 10/55:50 am -
1 stop6h 03m
Deal found 9/16![Delta logo]()
$579
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.
Thu 10/12:15 pm -
1 stop7h 35m
Mon 10/57:14 am -
2 stops8h 44m
Deal found 9/16![American Airlines logo]()
$735
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:15 pm -
2 stops31h 45m
Sun 10/116:49 am -
2 stops29h 40m
Deal found 9/16![United Airlines logo]()
$1,062
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 September 17, 2026.
Search for one-way flight options from Key West to Madison. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:59 am -
1 stop23h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$197
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:04 am -
3 stops32h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$221
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 12/3110:59 am -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Breeze Airways logo]()
$267
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.
Wed 10/2111:51 am -
1 stop5h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$357
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:59 am -
2 stops22h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Multiple Airlines logo]()
$379
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:35 pm -
2 stops11h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![United Airlines logo]()
$397
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:43 pm -
2 stops10h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![American Airlines logo]()
$407
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $356 (United Airlines) |
One-way from | $197 (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 September 17, 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
Wed 10/21
10:04 am-5:20 pm
3 stops32h 16m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$221
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Mon 10/26
10:59 am-4:18 pm
3 stops54h 19m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$264
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 12/31
10:59 am-5:30 pm
1 stop7h 31m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$267
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 12/4
4:10 pm-9:10 pm
1 stop6h 00m
Madison Truax Field
Sat 12/5
5:00 am-11:24 am
1 stop5h 24m
$356
Quickest round-trip
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Wed 10/21
11:51 am-4:27 pm
1 stop5h 36m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$357
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 11/13
5:07 pm-11:43 pm
1 stop7h 36m
Madison Truax Field
Mon 11/16
5:00 am-11:54 am
1 stop5h 54m
$377
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 12/4
11:43 am-4:30 pm
1 stop5h 47m
Madison Truax Field
Sat 12/5
1:32 pm-8:02 pm
1 stop5h 30m
$396
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 12/31
1:35 pm-11:40 pm
2 stops11h 05m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$397
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Wed 10/21
1:43 pm-11:12 pm
2 stops10h 29m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$407
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 10/1
11:42 am-4:20 pm
1 stop5h 38m
Madison Truax Field
Mon 10/5
5:50 am-12:53 pm
1 stop6h 03m
$579
Showing 1-10 of 11 resultsSorted 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 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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