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

Change your flight without a fee on select flights

Money Saving Bundle when you purchase Hotel + Flight! 

Get mobile alerts about flight delays, gate changes and more with the FREE Wotif app

Cheapest Flights from Madison (MSN) to Key West (EYW)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
American Airlines
American Airlines
American Airlines
American Airlines

Best Day to Book Flight from Madison (MSN) to Key West (EYW)

Madison to Key West Flight Information

Find the Cheapest Flights from Madison (MSN) to Key West (EYW)

Work hard, travel harder! Wotif brings you the cheapest Madison to Key West flights, making it possible to have a five star holiday without that five star price tag. Browse and compare our top MSN to EYW routes and airport options. So, go ahead and treat yourself, your sweetheart, or the kids to an unforgettable holiday this year.

to Information

Traveling From
Dane County Regional
Origin Airport
Origin Airport IATA Code
MSN
Traveling To
Key West Intl.
Destination Airport
Destination Airport IATA Code
EYW
Number of Airlines Serving
Average Flight Time
hours mins
Direct Flight Time
hours mins
Flight Price
NZ$685
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time zone:
America/New_York
Address:
4000 International Lane
Madison WI, 53704-3120
United States
IATA code:
MSN
Longitude:
-89.346497
Latitude:
43.136377
Time zone:
America/Chicago

Madison to Key West Flight Deals from NZ$685

Considering a quick trip to Key West, but not sure which is the best route for you? Well, you’re in luck! Wotif has done the hard work, so all you need to do is check out these flights from MSN to EYW. With heaps of cheap fares from Madison, we guarantee you’ll be arriving to your holiday destination in style without emptying your bank account in the process.

It’s easy to book flights to Key West from Madison  

For a huge choice of flights, simply enter your travel dates and hit search and we’ll hunt out fantastic deals on one-way, return and multi-city airfares to Key West from Madison from 10 different airlines. If you click the ‘direct flights’ box, you see flights that’ll get you to Key West in just hour(s) and mins, too.   

Snap up great deals on flights to Key West from Madison 

Choose from flights a day on average, with prices starting at NZ$685 and rising to NZ$769 depending on the cabin class, travel dates, and airline carrier. And if you’re up for a last-minute getaway, you can get great deals on flights from Madison to Key West today!  

Find cheap airfares to Key West from Madison 

Here are our insider tips for bagging a flight bargain: 

  • Look for midweek flights and late night, early morning arrival and departure times
  • Check out other airports near Madison and Key West
  • Avoid peak season (prices tend to be lower in February)
  • Be flexible with your travel dates and you can usually get cheaper options  

Reasons to book your flights to Key West from Madison with Wotif

Wotif is a super-easy way to find the best flight for you to Key West. Get more bang for your buck on flight and hotel or car rental combos and download the free Wotif app to tap into exclusive deals. Book now with Wotif and have a great flight!

 

Great places to stay after flight from Madison to Key West

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
The price is NZ$970 per night from 5 Mar to 6 Mar
NZ$970
5 Mar - 6 Mar
includes taxes & fees
Stay at this hotel in Key West. Enjoy free Wi-Fi, free parking and a snack bar/deli. Our guests praise the pool and the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (1,002 reviews)
Room was very clean. Pool and hot tub were a nice feature.

Reviewed on 31 Jan 2026

Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
The price is NZ$745 per night from 4 Feb to 5 Feb
NZ$745
4 Feb - 5 Feb
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,311 reviews)
Great staff, free water, free shuttle, right across from ocean, warm pool.

Reviewed on 1 Feb 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
The price is NZ$743 per night from 11 Feb to 12 Feb
NZ$743
11 Feb - 12 Feb
includes taxes & fees
Stay at this business-friendly resort in Key West. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8/10 Very Good! (1,004 reviews)
Flawless.

Reviewed on 2 Feb 2026

DoubleTree Resort by Hilton Grand Key - Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.