Kick off a celebratory summer night out at Boleo, perched atop the Kimpton Gray Hotel in the Loop. Once seated in the expansive space, enjoy shareable large-batch cocktails like Pisco Punch or The Fox Den. Come festival season, this enclosed rooftop lounge is also a popular spot among musicians, having played host to bands like Gorillaz and Deftones last summer. A new menu of Peruvian and Argentine fare complements the pulsing beats of Latin music. 122 W. Monroe St.
Esquire Champagne Room
Located on the third level of Del Frisco’s Double Eagle Steakhouse in the historic Esquire Theater, the opulent Esquire Champagne Room features 50 Champagnes and sparkling wines, more than 1,700 wines and a well-paired food menu encompassing caviar, oysters, foie gras mousse with apricot jam and lamb lollipops topped with romesco sauce. For a decadent evening, cozy up into a plush banquette and order classic white sturgeon caviar service alongside a bottle of 1998 Krug Brut Reims. 58 E. Oak St.
There’s glitz galore at this steak-heavy gem tucked away in newly renovated The Ritz-Carlton. An elegant cocktail can be daintily sipped at the ultramod, glamorous bar and sweeping lounge (the sidecar is a personal favorite), but it would be a mistake to overlook a sumptuous menu of expertly rendered steaks, toothsome appetizers and hefty pastas that can (and should) be enjoyed in the intimate dining room. 160 E. Pearson St.