Steps from Chicago’s top shopping district and across the river from the Loop, River North is smartly positioned as the city’s “where business meets pleasure” 'hood. The dining and drinking scene is an exciting amalgam of places suited for post-work imbibing and post-shopping refueling alike, including an ambitious cocktail bar and a posh, celebrity-owned steakhouse.
The cocktail menu at this State Street mainstay is so robust, it requires its own table of contents. Each chapter boasts a fanciful title, like Delicate Drams, Simple Wonders, and Dark Architecture, along with a selection of well-balanced drinks to choose from. Those who gravitate toward light, bright cocktails will enjoy the gin-based War of the Roses with Pimm’s, lime, elderflower, mint, and Peychaud’s bitters, while East of Omaha, a full-bodied concoction of Larceny bourbon, Laphroaig, port, vanilla, and chocolate bitters, will appeal to those who prefer bold sips. 505 N. State St., 312-755-9704
When a Japanese noodle craving hits, stop at this lively eatery for a variety of noodle-based dishes, such as the spicy Tan Tan Men ramen with a pork meatball, pork chashu, pork miso, bok choy, and bean sprouts. And thanks to the latest menu addition, red curry-coconut udon loaded with okra, a medley of Japanese mushrooms, hominy, chickpeas, and eggplant, vegetarians can get their noodle fix, too—sans pork broth. 116 W. Hubbard St., Chicago, 312-64-0466
Drink away a case of the Mondays at this subterranean tiki hideaway. The bar, accessible through the back alley behind Bub City, is home to several large-format cocktails designed to share, and span from the spectacular Treasure Chest No. 2 with aged Jamaican rum, blackberry, pomegranate, pineapple, lemon, Falernum, and an entire bottle of Dom Perignon, to the relatively modest Pieces of Eight, a breezy mix of light Caribbean rum, passion fruit, lemon, and Falernum. Soak up the rum with sharable small bites, such as coconut shrimp, Polynesian spare ribs, and luau chips with pineapple guac. 435 N. Clark St., 312-610-4220
For killer steaks and a see-and-be-seen vibe, nothing trumps seriously buzzy, part-Rancic-owned RPM Steak. The space bucks the conventional, stodgy steakhouse look for one that’s decidedly more sophisticated: Mahogany paneling, ivory curtains and chairs, and servers bustling about in sharp white jackets—and we love it. Steaks range from sliced hangar steak to a big-ticket 48 oz. center cut Porterhouse, and pair well with popular sides like pillowy Parker House rolls with rosemary Nordic butter, thick-cut bacon brushed with bourbon-vanilla bean glaze, and the classic Iceberg wedge salad. 66 W. Kinzie St., 312-284-4990
Seemingly endless lines stand as a testament to both the popularity and the greatness of this fried dough emporium. The shop—a tiny storefront marked by a story-tall menu painted on the exterior—bakes a set number of doughnuts daily; once the supply runs out, the shop closes. Your best bet is to either stop by early to get your fill of dense, supremely sweet old-fashioned doughnuts in an array of flavors, like buttermilk, pistachio, and lemon-poppy seed, or to track the shop’s food truck on social media to see if it rolls into your neighborhood. 401 N. Franklin St.
Thanks to a state-of-the-art retractable roof and two-level fire pit, this chic lounge on the fourth floor of The Godfrey Hotel is the ideal place to get a buzz on and take in sweeping city views regardless of the weather. Even the drinks are elevated: While most chefs leave the cocktail-making to the bartenders, chef Riley Huddleston likes to prepare special Chef Cocktails himself, like the Chef’s Margarita with fresh juices, Don Julio, Cointreau, Cointreau Noir, and Tuaca with a signature habanero salt air foam. 127 Huron St., 312-649-2000
From pork-fried almonds with rosemary and garlic to pig’s tails braised in balsamic with grated egg and parsley, porcine eats is the name of the game at this small-plates destination. Not feeling pork? Try the fall-off-the-bone tender turkey leg confit with crispy lentils, treviso, endive, and agrodolce or the Wagyu sirloin tip drizzled in a bone marrow vinaigrette. Pro tip: The restaurant doesn’t accept reservations, so try to stop in right when it opens or at an off time in order to snag a seat. 500 N. Michigan Ave., 312-464-1744
Authentic Peruvian flavors pervade chef Jesus Delgado’s menu at this vibrant escape, transporting guests to South America by way of tiraditos, cebiches, and causitas. Noteworthy dishes include the impossibly fresh ahi tuna tiradito with passion fruit leche de tigre, honey, and chifa sauce; tender octopus skewers with chimichurri, fried garlic, and olive sauce; and hearty pork fried rice. Wash it all down with a selection from the pisco-soaked beverage program, such as the Lima Llama with Barsol Quebranta pisco, lime, and ginger beer and a Peruvian riff on the classic Moscow Mule. And whatever you do, don’t miss the traditional alfajores for dessert. 118 W. Grand Ave., 312-222-9700
Perched on the 16th floor of Trump International Hotel & Tower, Michelin-starred Sixteen manages to successfully reinvent itself every season while never allowing the caliber of its food and service to waver. Each seasonal dining experience is built around a specific theme, such as Faces of Sixteen and Food in Progress, that flows through the multi-course tasting menu, the atmosphere, the plating, and the information delivered to guests by the front-of-house staff. 401 N. Wabash Ave., 312-588-8030
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