Old Town has plenty of history, but don't expect anything outdated in the neighborhood just north of the Gold Coast. An Old Town address is a signature of success in Chicago. Elegant townhomes from the 1800s sit next to modern mansions built over the past decade.
You don't have to live here to enjoy this North Side neighborhood, though. Residents from nearby Lincoln Park head south to celebrate on Wells Street at bars like Old Town Social and Benchmark. For a dose of laughter from Chicago's most well-known comedy spot, head to Second City. The improv club has been home to John Candy, Jim Belushi, Bill Murray and a mile-long list of some of the funniest TV and movie personalities of the past 50+ years.
If you're looking for something more serious, head west to Halsted Street for a play at Steppenwolf Theater. Music fans also head to Old Town for an intimate environment at Park West for mid-size performances. After the show, head to Vintage 338 to wind down with wine and cheese.