$157+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Oct 11 — Oct 181
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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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 11, 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 11, 2026.
This Delta deal was found by Cheapflights users on 9/10. 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 9/10![Delta logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/110:59 am -
1 stop7h 21m
Wed 10/710:38 am -
1 stop23h 43m
Deal found 9/8![Breeze Airways logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/44:45 pm -
1 stop8h 14m
Sat 12/59:15 am -
2 stops7h 41m
Deal found 9/10![American Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 9/8. 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
Wed 10/75:00 am -
2 stops10h 11m
Deal found 9/8![American Airlines logo]()
$585
This United Airlines deal was found by Cheapflights users on 9/10. 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 12/412:41 pm -
1 stop6h 05m
Sat 12/53:49 pm -
3 stops21h 47m
Deal found 9/10![United Airlines logo]()
$589
This United Airlines deal was found by Cheapflights users on 9/9. 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 12/1612:41 pm -
1 stop6h 05m
Thu 12/176:05 am -
1 stop7h 18m
Deal found 9/9![United Airlines logo]()
$652
This United Airlines deal was found by Cheapflights users on 9/10. 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 12/212:41 pm -
1 stop7h 47m
Thu 12/35:00 am -
1 stop5h 11m
Deal found 9/10![United Airlines logo]()
$657
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/10![American Airlines logo]()
$695
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 11, 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 11, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. 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 1/155:51 pm -
1 stop6h 19m
Sun 1/176:00 am -
1 stop7h 08m
Deal found 9/10![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/10. 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 9/10![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/8. 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
Wed 10/75:00 am -
2 stops10h 11m
Deal found 9/8![American Airlines logo]()
$585
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/145:49 pm -
1 stop7h 36m
Fri 1/157:07 pm -
1 stop15h 29m
Deal found 9/10![American Airlines logo]()
$622
This KAYAK deal was found by Cheapflights users on 9/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:59 am -
3 stops47h 59m
Wed 10/710:38 am -
3 stops22h 41m
Deal found 9/8![Breeze Airways logo]()
$1,273
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.
Tue 12/14:53 pm -
1 stop8h 06m
Wed 12/28:05 am -
1 stop6h 01m
Deal found 9/11![American Airlines logo]()
$715
This American Airlines deal was found by Cheapflights users on 9/9. 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 12/161:52 pm -
2 stops9h 36m
Thu 12/178:28 am -
2 stops9h 53m
Deal found 9/9![American Airlines logo]()
$812
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/210:18 am -
2 stops10h 49m
Thu 12/36:02 am -
2 stops9h 12m
Deal found 9/10![American Airlines logo]()
$812
This United Airlines deal was found by Cheapflights users on 9/7. 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 -
1 stop7h 00m
Sun 10/1111:15 am -
1 stop25h 14m
Deal found 9/7![United Airlines logo]()
$1,636
Last-minute flights from Key West to MadisonDiscover last-minute flight deals from Key West to Madison. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Madison. Data last updated September 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/110:59 am -
1 stop7h 21m
Wed 10/710:38 am -
1 stop23h 43m
Deal found 9/8![Breeze Airways logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/8. 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
Wed 10/75:00 am -
2 stops10h 11m
Deal found 9/8![American Airlines logo]()
$585
This United Airlines deal was found by Cheapflights users on 9/7. 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 -
1 stop7h 00m
Sun 10/1111:15 am -
1 stop25h 14m
Deal found 9/7![United Airlines logo]()
$1,636
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 11, 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 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 1/1512:59 pm -
1 stop21h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 1/2012:19 pm -
3 stops30h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$276
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/205:49 pm -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/10. 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 1/159:52 am -
2 stops9h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$415
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 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (United Airlines) |
One-way from | $157 (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 11, 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
Fri 1/15
12:59 pm-9:58 am
1 stop21h 59m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Fri 1/15
5:51 pm-11:10 pm
1 stop6h 19m
Madison Truax Field
Sun 1/17
6:00 am-2:08 pm
1 stop7h 08m
$339
Quickest round-trip
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Wed 1/20
5:49 pm-12:25 am
1 stop7h 36m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$348
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
$376
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 10/1
2:15 pm-8:50 pm
1 stop7h 35m
Madison Truax Field
Wed 10/7
5:00 am-4:11 pm
2 stops10h 11m
$585
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 1/14
5:49 pm-12:25 am
1 stop7h 36m
Madison Truax Field
Fri 1/15
7:07 pm-11:36 am
1 stop15h 29m
$622
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Tue 12/1
4:53 pm-11:59 pm
1 stop8h 06m
Madison Truax Field
Wed 12/2
8:05 am-3:06 pm
1 stop6h 01m
$715
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Wed 12/16
1:52 pm-10:28 pm
2 stops9h 36m
Madison Truax Field
Thu 12/17
8:28 am-7:21 pm
2 stops9h 53m
$812
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Wed 12/2
10:18 am-8:07 pm
2 stops10h 49m
Madison Truax Field
Thu 12/3
6:02 am-4:14 pm
2 stops9h 12m
$812
Key WestMadison
EYW Key West - MSN Madison Truax Field
EYWMSN
Key West
Thu 10/1
10:59 am-9:58 am
3 stops47h 59m
Madison Truax Field
Wed 10/7
10:38 am-10:19 am
3 stops22h 41m
$1,273
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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