CHICAGO CUT STEAKHOUSE
Drawing a high-profile crowd ranging from government types to visiting celebs and local athletes, this sleek riverside destination from industry vets David Flom and Matt Moore has risen to become one of the city’s most popular restaurants—and with its spoton service and primo steakhouse fare (the decadent “lobsterscargot” is lifechanging), it’s no wonder. 300 N. Lasalle St., 312-329-1800; chicago cutsteakhouse.com
This buzzing terrace atop the landmark Chicago Athletic Association Hotel has been among the hottest tables in town since its 2015 opening, thanks to Christian Ragano’s creative cuisine and killer year-round views of Millennium Park.
INSIDER TIP: Lunch is a much easier reservation—and boasts one of the best duck confits in the city. 12 S. Michigan Ave.,13th Fl., 312-7923502; cindysrooftop.com
COCO CHAMPAGNE LOUNGE
Nightlife impresario Andy Li (TR Napa Valley) returns with this new addition to Hubbard Street’s red-hot dining and drinking scene: a posh, multilevel restaurant and wine bar in the heart of River North. 23 W. Hubbard St.; cocochampagnelounge.com
THE FLAMINGO RUM CLUB
From Caribbean-inspired tapas to luxe bottle service and a bar serving up mojitos, daiquiris, and caipirinhas, this island-focused restaurant and cabaret aims to bring the spirit of Havana to River North.
INSIDER TIP: Wednesdays feature a can’t-miss cabaret starting at 9 PM.
601 N. Wells St., 312-929-0060; theflamingorumclub.com
Eclectic, clubby décor, smart craft cocktails, and a globe-spanning menu of dishes like duck fatpoached scallops, lamb meatballs, and lobster deviled eggs make this a Hubbard Street favorite. 110 W.