$180 Cheap Flights from Madison (MSN) to Key West (EYW)

View $180 flight on Mon, Nov 24, 2025Opens in a new window

Popular airlines from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)

Cheap Flights from Madison to Key West (MSN-EYW)

Prices were available within the past 7 days and start at $180 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Jan 18 - Wed, Jan 28
MSN
Madison
EYW
Key West
$259 Roundtrip, found 17 hours ago
$259
Roundtrip
found 17 hours ago
Select Delta flight, departing Sun, Jan 18 from Madison to Key West, returning Wed, Jan 28, priced at $259 found 17 hours ago
American Airlines
Thu, Jan 1 - Tue, Jan 6
MSN
Madison
EYW
Key West
$264 Roundtrip, found 5 hours ago
$264
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Jan 1 from Madison to Key West, returning Tue, Jan 6, priced at $264 found 5 hours ago
Delta
Sun, Jan 18 - Tue, Jan 27
MSN
Madison
EYW
Key West
$264 Roundtrip, found 17 hours ago
$264
Roundtrip
found 17 hours ago
Select Delta flight, departing Sun, Jan 18 from Madison to Key West, returning Tue, Jan 27, priced at $264 found 17 hours ago
United
Tue, Sep 1 - Sat, Sep 5
MSN
Madison
EYW
Key West
$269 Roundtrip, found 15 hours ago
$269
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Sep 1 from Madison to Key West, returning Sat, Sep 5, priced at $269 found 15 hours ago
American Airlines
Fri, Jan 23 - Tue, Jan 27
MSN
Madison
EYW
Key West
$269 Roundtrip, found 16 hours ago
$269
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Jan 23 from Madison to Key West, returning Tue, Jan 27, priced at $269 found 16 hours ago
American Airlines
Fri, Feb 6 - Mon, Feb 9
MSN
Madison
EYW
Key West
$274 Roundtrip, found 16 hours ago
$274
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Feb 6 from Madison to Key West, returning Mon, Feb 9, priced at $274 found 16 hours ago
American Airlines
Tue, Mar 31 - Wed, Apr 8
MSN
Madison
EYW
Key West
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Mar 31 from Madison to Key West, returning Wed, Apr 8, priced at $276 found 2 days ago
American Airlines
Sat, Jan 24 - Sat, Jan 31
MSN
Madison
EYW
Key West
$279 Roundtrip, found 15 hours ago
$279
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Sat, Jan 24 from Madison to Key West, returning Sat, Jan 31, priced at $279 found 15 hours ago
American Airlines
Fri, Jan 23 - Tue, Jan 27
MSN
Madison
EYW
Key West
$281 Roundtrip, found 16 hours ago
$281
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Jan 23 from Madison to Key West, returning Tue, Jan 27, priced at $281 found 16 hours ago
American Airlines
Tue, Feb 3 - Mon, Feb 9
MSN
Madison
EYW
Key West
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Feb 3 from Madison to Key West, returning Mon, Feb 9, priced at $289 found 2 hours ago

Find the cheapest month to fly from Madison (MSN) to Key West (EYW)

April is typically the cheapest month to fly

From $219 - $633 per traveler.

Alternative airports near Key West

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Key West Intl. EYW. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $304
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $304

Frequently asked questions

How much does a flight from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW) cost?
Lock in a cheap one-way flight from $180 or cheap return flight from $259 from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)?
January is the least expensive month to fly from MSN to EYW. Planning your trip for the off-season is often the key to finding better deals on flights.
What is the cheapest airline that flies from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from MSN to EYW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)?
There are no daily nonstop flights from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from MSN to EYW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)?
Choose a flight from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW) that leaves before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW) last-minute?
Holding off until just before your departure to book a flight from MSN to EYW often results in higher prices. While you may come across some last-minute deals, they aren't always guaranteed. Allow some flexibility in your schedule to maximize your chances of landing a bargain.
Is it cheaper to book a MSN to EYW flight and hotel package?
You'll generally save money by booking a MSN to EYW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After choosing your preferred accommodations and flights, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Dane County Regional Airport (MSN) to Key West Intl. Airport (EYW)?
Usually, it's possible to reschedule or cancel your MSN to EYW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Dane County Regional
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$258
Distance
1354 mi

Book with confidence

Madison to Key West Flights

The cheapest times to fly from Madison to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Madison to Key West are during the month of January. You can find some of the cheapest flights from Madison to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Madison to Key West

Sunday is one of the best days to book for cheap flights from Madison to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Madison to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Madison to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $180 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Madison to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Madison to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Madison to Key West Flights

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*Available to One Key members.