111 W Kinzie St (btwn N LaSalle St & N Clark St), Chicago, IL
Restaurant · River North · 141 tips and reviews
Eater: This 1920s-era speakeasy offers a swank lounge, private cabanas, live entertainment space and an enormous whiskey library with over 300 choices.
Roof Deck · Old Town Triangle · 73 tips and reviews
Eater: Enjoy the view from the rooftop patio or the glass-enclosed space in the winter, with comfy couches, high-top tables and bar seating, it's a big draw for Erin Hayes' destination-themed cocktails.
Cocktail Bar · Fulton Market · 175 tips and reviews
Eater: Charles Joly leads the beverage program and has been turning over the cocktail list. Sit on the patio on a nice night or try your luck and see if you can get into the exclusive Office underneath.
Eater: Step inside the intimate space and peruse through an extensive handcrafted drink menu that includes vodka, tequila, rum, brandy and portable bitters creations. Try the Juliet & Romeo or the Sazerac.
Cocktail Bar · Streeterville · 78 tips and reviews
Eater: You will have no problem bellying up to the bar at this modern restaurant and culinary cocktail lounge with an unmatched drink program, led by Cristiana DeLucca.
201 E Delaware Pl (at Mies van der Rohe Way), Chicago, IL
Cocktail Bar · Streeterville · 68 tips and reviews
Eater: Add this to the list of downtown rooftop spaces with a hip, modern terrace atop the Raffaello Hotel. The menu features a mix of seasonal cocktails along with a focus on bourbon and whiskey.