Will and the entire Banks family vacation in Will's hometown, Philadelphia and learn a surprising secret about Will's reputation in the neighborhood. Will tells Carlton about a dangerous gang leader called Omar, who Will is determined to fight. Will learns that Omar has grown up and so should he. Will stays behind with his mother for the season finale (which was intended to be the series finale, before NBC renewed the series again).
Will and the Banks family vacation to Will's hometown in Philadelphia where Will learns to his horror that he has a reputation as a chicken due to not fighting Omar, a local bully and instead going to live in Bel-Air. To salvage his reputation, Will plans to fight Omar on the basketball court where he had the notorious fight but finds that Omar is no longer a bully and has grown up, attempting to give back to his community and help people. Will refuses to take no for an answer and keeps trying to fight Omar, who reminds Will that he needs to grow up and stop worrying about his reputation. Will chooses to stay home an extra week with Vy but later calls Uncle Phil to tell him that he's not coming back.
- Omar was the bully who was spinning Will around the credits at the basketball court, that made his mom send him to live with his Uncle and Aunt in Bel-Air, California.
- The Max diner from Saved by the Bell serves as the set for the Philly diner where they serve the “Chicken Will sandwich”
- Geoffrey sliding out in his underwear and socks as well as the accompanying song "Old Time Rock and Roll" by Bob Seger is a reference to the film Risky Business.