333 N. Michigan Ave.

This Art Deco skyscraper is one of four landmarks flanking the Michigan Avenue bridge, characterized by upper-level setbacks conforming to a then-new zoning law. The building's long, narrow profile and solid massing are thought to pay tribute to the Monadnock - and also make great use of natural lighting. The building's famous Tavern Club hosted regulars including Frank Lloyd Wright, Carl Sandburg and William Wrigley. A recent $50 million renovation has ushered in LEED Silver certification and a full-floor amenity suite with a new Tavern Club lounge, conference and fitness facilities, and more.

Holabird & Root, 1928; Eastlake Studio interior: Eastlake Studio, 2018