Distance from downtown: 7.2 miles Via: Red Line Best for: Performing arts, historical architecture Go: Evening
GREEN MILL COCKTAIL LOUNGE Buildings about as old as Al Capone are lucky to see a few adaptive reuses before demolition, but the Green Mill has hardly changed at all. The infectious energy of this famous Prohobition-era establishment is undiluted in the years since Chicago’s notorious mobsters sidled up to the bar. The jazz is top-notch, as are the poetry slams every Sunday. Come early; the place is packed with loyal longtime regulars.
GRACELAND CEMETERY Chicago’s formidable architectural legacy lies beneath this Gilded Age-era cemetery’s 119 sprawling green acres. Don’t miss Daniel H. Burnham’s solitary resting place on a wooded lake isle, Louis Sullivan’s gorgeous rough-hewn headstone, and Ludwig Mies van der Rohe’s unsurprisingly austere black granite slab.
FOUNTAINHEAD The ever-changing menu of pub fare is creative, but dressed-down—think sriracha deviled eggs, house beer sausage, and mezcal-marinated chicken tacos. The food is from scratch, supplied by the chef’s own garden and his favorite regional farms, and accompanied by a lengthy list of craft brews. And in summer, you won’t find a better rooftop for dining in all of Uptown.
BLACK ENSEMBLE THEATER The sleek, LEED-certified Black Ensemble Theater is a sight for contemporary eyes in this neighborhood of elevated train tracks. The exterior makes an elegant interplay of contemporary materials, combining the verticality of ipe wood paneling with sturdy horizontal cement-block panels, red brick, and the glass curtain wall.
UPTOWN THEATRE BUILDING Amid talks of reviving Uptown’s legacy as an entertainment district, this grand old movie palace sits at the center of the conversation. The vast interior was touted as “An Acre of Seats in a Magic City” during its grand opening in 1925—it boasts a higher square footage than even New York’s Radio Music Hall. But the Rapp and Rapp-designed landmark, with its unique colonnaded eight-story façade, has been out of commission for decades and needs $70 million of restoration.