Most Indulgent Cocktail
Slap down a crisp Benjamin at Z Bar for a taste of the Manhattan Royale, made with 18-year Elijah Craig bourbon or 15-year WhistlePig rye. A gold-laced ice cube tops off this sipper you can’t sip anywhere else. 108 E. Superior St.
Best Caviar Service
At Heritage Restaurant & Caviar Bar, the menu is sprinkled with roe and caviar accents, but caviar service itself features everything from Belgian gold osetra ($205 for 30 grams) to hackleback ($85). Can’t decide? The Grand Caviar Platter puts your picks in safe hands. 2700 W. Chicago Ave.
Best Way To Have It All
With the new Steakmanship Series at Michael Jordan’s Steak House, there’s no need to choose. The Legendary Flight ($250) features not only filet mignon, dry-aged wagyu and a 10-ounce New York strip, but broiled lobster tail, foie gras and king crab to wash it all down. 505 N. Michigan Ave.
Best Place to Start Your Natural Wine Journey
Visit Roostock Wine & Beer Bar and chat up co-owner Jamie McLennan, whose expertise in unfiltered, natural winemaking will get you up to speed—and up for sipping—in no time. 954 N. California Ave.
Most Curated Chocolatier
Vosges Haut-Chocolat is known for its ever-evolving collections of truffles and chocolate bars, thanks to the creativity of owner Katrina Markoff. 520 N. Michigan Ave.; 951 W. Armitage Ave.
Most Over-the-Top Dinner—Literally
Head to the dome-esque cupola atop LondonHouse Chicago for a perfectly curated meal of up to 20 courses for up to $1,000 per person, which means the sky is truly the limit. 85 E. Wacker Drive
Best Old-School Power Lunch
Adorned with fine art and handsome wood accents, RL Restaurant is a ritzy spot to be seen, while menu items like dover sole, calf’s liver and a wagyu beef hot dog get right down to business. 115 E. Chicago Ave.
Most Decadent Meal For Vegans
Brass Heart chef Matt Kerney says his 15-course vegan tasting menu ($145 per person) was his most challenging, making for a meal where meat is never missed. 4662 N. Broadway