Bar Sótano

Below Rick Bayless' iconic Frontera Grill is a mood-lit mezcalería serving up agave-based cocktails and upscale Mexican bar bites. Bar Sótano's menu takes inspiration from traditional Mexican markets, where items are organized based on flavor profiles. Go for the Mango, Chamoy from the ripe and juicy Fruit Stand section, or try the serrano-cucumber margarita from the bold and spicy Chile Stall. The bar itself boasts a vibrant mural and an enigmatic atmosphere dimmed with flickering candles—enjoy and sip away. 443 N. Clark St., barsotano.com

The Darling

A flower shop conceals the entryway to the handsome lounge at The Darling—owner Sophie Huterstein's way of delighting guests from the very start. “I'm a big believer in giving little gifts,” she says. These gifts emerge in part as wonderfully strange performances by belly dancers, magicians and vaudeville acts sprinkled throughout the venue. Drinks play on English classics, and the tapped wine system serves glasses at a single price point. If you fancy a livelier atmosphere, head upstairs to the thrumming bar. 905 W. Randolph St., thedarlingchi.com

Mordecai

Wrigleyville has long been a bucket-list visit for tourists, but recent additions of upscale spots beckon to locals just as much. Mordecai sits directly across from Wrigley Field, and invites fans to catch game-day vibes while tasting rare bourbon and taking in the surrounding vintage baseball decor. The new second floor speakeasy, Hush Money, was named for the attempted bribe of famed Cubs pitcher Mordecai Brown, and the bar shakes up craft cocktails on a patio perfect for postgame celebrations. 3632 N. Clark St., mordecaichicago.com

Kumiko

Inventive drinks with subtle nuances delight at Julia Momose's Japanese-inspired Kumiko. Flights feature a cocktail pour alongside tastings of the intricate sakes and teas she incorporates in the drink, while sophisticated spirit-frees provide a delicious experience for everyone. Taste your way through a memory with the New Wave, inspired by karē raisu and chilled barley tea—a cooling summertime combo Momose enjoyed as a child in Japan. It's a culinary approach to cocktailing in a serene space by a team envisioning an awakened drinking experience. 630 W. Lake St., barkumiko.com