Notable Chicagoans call the South Shore neighborhood their childhood home. Undoubtedly they spent time at Rainbow Beach, one of the city’s largest beaches. The park there offers one of the best views of Chicago’s skyline. This South Side neighborhood is best explored in the daytime. You’ll get an unfettered glimpse at a variety of architectural styles in both its residential homes and larger structures. Landmarks like the New Regal Theater built in the style of a Moorish theater and Saint Philip Neri Roman Catholic Church with its Tudor-revival influences are visually arresting. Take a short stroll through the landmark Jackson Park Highlands District for a taste of unique early 20th-century urban planning and large mansions. The South Shore Cultural Center is yet another unique structure and treasure in Chicago’s arts and culture community, complete with galleries, studios, a golf course, and a 600-seat theater.