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
Most Luxuriant Sushi Experience
Katana has it all: L.A. breeding, a sultry dining room and an omakase experience from accomplished chef Masa Adachi. 339 N. Dearborn St.
Most Over-the-Top Seafood Tower
The seafood tower ($140) at Free Rein boasts massive king crab claws, colossal prawns and roe-topped crab salad—making it pretty clear why this tower is meant for four. 230 N. Michigan Ave.
The Best Place to Save Room for Dessert
It’ll be a challenge, since nearly every plate at Pacific Standard Time is immensely satisfying, but do make sure to sample pastry chef Natalie Saben’s creative sculptural desserts next time you stop by. 141 W. Erie St.
Best Room With A View
While the dishes at Gibsons Italia are showstoppers in their own right, dinner includes dazzling views of the Chicago River too. 233 N. Canal St.
Best Celeb Spotting
Both RPM Steak and RPM Italian are great spots for a swanky night out, but they’re also often packed with a who’s who of local and national notables. Recent guests included the cast of Shameless, former President Bill Clinton and rapper Drake. 66 W. Kinzie St.; 52 W. Illinois St.
Best Rare-Spirits Destination
Located inside Wrigleyville’s Hotel Zachary, Mordecai is home to one of the city’s most extensive vintage and hard-to-get spirits collections, including what’s touted as one of the country’s largest Pappy Van Winkle roundups. 3632 N. Clark St.
Best Way To Step Up Your Sunday Brunch Experience
Prime & Provisions
Nothing is held back at this steakhouse’s premium Sunday brunch. All the favorites—eggs Benedict, 2-inch-thick housemade bacon, carved prime rib—are laid out in a dazzling spread fit for kings. Chefs stand ready to prepare made-to-order omelets with fillings like asparagus, filet tips and goat cheese, or drizzle a bevy of sauces, syrups and toppings on freshly pressed Belgian waffles. But the pièce de résistance is the tableside mimosa service, which can include bottomless 2009 Dom Pérignon brut ($250 per person) paired with seasonal juices and purees. Guava blood-orange mimosa, anyone? $59 for adults, $15 for children, 222 N. LaSalle St.
Best Chef’s table experience
Akin to seeing Monet put brush to canvas, the Kitchen Table at Alinea is a chance to watch the masters at work from a glass-encased dining room sure to garner amazement before the first bite. 1723 N. Halsted St.
Best Sommelier You Haven’t Met Yet
From his start at Charlie Trotter’s, Ervin Sandoval’s career as a sommelier spans 30 years. At Benny’s Chop House, he has amassed a collection of 10,000 bottles—including rarities like a 1945 Chateau d’Yquem. 444 N. Wabash Ave.
Best MultiCourse Tasting Menu
Acadia holds nothing back, with a vastly shifting eight-course seasonal tasting menu ($165) comprised of extraordinarily complex dishes. 1639 S. Wabash Ave.
Most Extensive Wine Cellar
When the wine for three individual restaurants is flowing from one cellar, Italian Village Restaurants has stocked up to ensure satisfaction for all, with more than 30,000 bottles and counting. 71 W. Monroe St.