Cheap flights from Madison to Key West from $284

Travelers frequently search for route combinations, such as Madison and Orlando, Portland, Fort Myers, Puerto Vallarta, Chicago, Cancún, Seattle, Fort Lauderdale, Lower Prince's Quarter, Tampa, Nashville, San Juan, Paris, Washington, D.C., Manama, Kabul, San Francisco, Puerto Maldonado, Rajkot, Istanbul.

Travelers frequently search for route combinations, such as Key West and Orlando, Tampa, Minneapolis, Fort Lauderdale, Detroit, Philadelphia, Washington, D.C., Nashville, Indianapolis, Cincinnati, Atlanta, Portland, Providence, Fort Myers, New York, Plattsburgh, Charlotte, Asheville, Norfolk, Atlantic City.

The main airport in Madison is Dane County Regional. It is also served by O Hare International, Chicago Midway International, General Mitchell International, Appleton International, Chicago Rockford International, The Eastern Iowa, Dane County Regional, Quad City International, Green Bay–Austin Straubel International, Central Wisconsin.

The main airport in Key West is Key West International. It is also served by Miami International, Key West International.

Currently, you can fly between Madison and Key West with United Airlines, Silver Airways.

If you don’t have specific dates for your trip between Madison and Key West, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Madison and Key West, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around Madison. The main one is Dane County Regional and other nearby airports include O Hare International, Chicago Midway International, General Mitchell International, Appleton International, Chicago Rockford International, The Eastern Iowa, Dane County Regional, Quad City International, Green Bay–Austin Straubel International, Central Wisconsin

There are a number of airports in and around Key West. The main one is Key West International and other nearby airports include Miami International, Key West International.