• Noble-Seymour-Crippen House (1833, oldest building in Chicago)
• Wingert House
• William Howard Taft High School
• Norwood Park Historical District (National Register of Historic Places)

Old Norwood preserves the original village core of Norwood Park, platted in 1868 and named for Henry Ward Beecher's novel Norwood, or Village Life in New England. Incorporated as an independent village in 1874, it retained its own government for nearly two decades before voters approved annexation to Chicago in 1893 by a wide margin. Its curvilinear streets, unusual for Chicago's grid-based city, survive intact from that original village plan.

The Noble-Seymour-Crippen House, built in 1833 and expanded through the 1850s, is the oldest standing building in Chicago — spared from the Great Chicago Fire of 1871 only because Norwood Park was still an independent village well beyond the blaze's reach. The Wingert House and William Howard Taft High School, the inspiration for the musical Grease, round out the historic district recognized by the city in 1986.

From the oldest house in Chicago to the high school that inspired a Broadway classic, Old Norwood wears its village-turned-city-neighborhood history plainly — worth carrying with you long after you've left its curved streets.