From artsy to affluent, this historic neighborhood has been home to people from all walks of life over the years. An incredibly popular neighborhood destination, largely because of its close proximity to the lake and downtown, Old Town keeps up a lively pace day and night. Victorian-era buildings, brick alleyways and narrow, tree-lined streets are charming backdrops to a busy main strip that runs along Wells Street between North Avenue and Division Street.

For entertainment, comedy takes center stage—with The Second City and Zanies Comedy Club providing the laughs—and the resident theater scene is stellar as well. Shopping is quite eclectic as you can pick up specialty spice blends, imported olive oils, chunks of fudge, rare wines and premium cigars all in one single spree down Wells.

Family-owned restaurants are fixtures of the neighborhood and the depth of the variety runs deep: barbecue ribs, sushi, steak frites, pasta and pizza are all noteworthy. You can continue to soak up area history at one of the more seasoned taverns, though new bars and boutiques keep Old Town forever young and hip.