As well as starring in The Love Boat, Whelan made numerous guest appearances in TV shows including Fantasy Island (twice), Vegas, Trapper John, M.D., Matt Houston and Battle of the Network Stars. In late 1979, she played the role of Lisa Davis, a heart patient, in Airplane!

In 1984, Whelan graduated from the Buckley School in Sherman Oaks, California (a close friend of classmate Laura Dern) with a stint at Guildford College in Surrey, England where she studied English Literature before coming back to Los Angeles.

Whelan met her first husband, Brad St. John, as an associate producer for UPN News in Los Angeles, shortly after leaving Madison Square Garden. They married in December 1993. Soon after their wedding, she became pregnant with their first son, Harrison. Whelan divorced St. John in 2001.

In 1999, Whelan left acting and started working as an investigative producer at the Los Angeles television station KCOP and continued as a radio show host for 1210 WPHT radio.

On November 25, 2001, Whelan appeared on an episode of The Weakest Link, a trivia game show hosted by Anne Robinson. Whelan competed against other celebrity TV stars, including Mackenzie Phillips, Nell Carter, Cindy Williams, Joan Van Ark, Erin Moran, Erik Estrada, and Fred “Re-run” Berry. She outlasted the others, winning $57,000 for her charity.

Returning to the East Coast, she married her second husband, Mike Chaykowsky, in April 2004. Her second son, Grant, was born in 2006. In 2014, Whelan filed for divorce from Chaykowsky and moved back to Los Angeles in 2012, where she lives and raises her two sons.

On September 10, 2008, Whelan appeared with several other cast members from the movie Airplane! in a reunion segment on NBC’s the Today Show. In October 2008, Whelan made her New York City cabaret debut with her one-woman show Jill Whelan: An Evening In Dry Dock at The Metropolitan Room. From September to November 2011, Whelan appeared in the British farce Move Over Mrs. Markham at Stage West Theatre Restaurant in the Toronto, Ontario area.

Whelan was set to replace Mark Thompson, who retired on August 17, 2012, after 25 years co-hosting The Mark & Brian Show on KLOS in Los Angeles, but during Thompson’s final broadcast, co-host Brian Phelps announced that he, too, was quitting KLOS.

In 2013, Jill moved on as co-host with Brian Phelps in The Brian And Jill Show. Whelan and Phelps share a love for improvisational comedy, and have created hundreds of characters together that they have performed both on the stage during improvisation shows and in sketches performed on their podcast.

In 2015, Whelan was hired by Princess Cruises as a celebrations ambassador.