The Best Day-Drinking Spots in Chicago

A little slice of Austin in Wicker Park, Big Star is about as country as Chicago gets—which is to say, not very. Vintage neon and a vinyl soundtrack are the only hints of kitsch at this 1940s gas station-turned-taqueria, whose garage doors open onto one of the most popular patios in town. Tacos and tequila are the stars here; craft cocktails are deliciously pretense-free, and a well curated selection of whiskey and craft beers make a great case for whiling the afternoon away.

Perched on the top floor of the Chicago Athletic Association Hotel, Cindy’s is the rare rooftop hotel bar that serves “potions and elixirs” worth remembering, thanks to Spirit Guide Nandini Khaund, who came up at the Violet Hour and Big Star. For the most part, the scene is still, well, scene-y, but especially on a clear day, the nonpareil views are worth every pretty penny.

Truly an all-day café, Estereo is modeled after the coffee/cocktail concepts commonplace in Latin America, with a soundtrack and style to match. It’s pitched on a quirky triangular corner that inspired the bar’s design team to cover both street-facing walls in garage-style roll-up doors, maximizing daylight and people-watching. When the weather’s good, those doors roll up to let in a breeze, and the agave spirit–centric menu goes down dangerously easy. But even when Chicago winters are at their worst, Estereo somehow maintains a permanently breezy air (see What to Drink).

The cheap-and-chic, finger-lickin’-good sister restaurant to Longman & Eagle, Parson’s was an instant classic from the minute it opened in the summer of 2013. Situated on a high-traffic corner of Humboldt Park with a 1977 El Camino parked permanently in the lot, the building itself is tiny, seating less than 30. But the patio is like an adult play lot complete with gravel grounds and table tennis, where hours can be whiled away simply people watching over round after round of Negroni Slushies and Stiegl Radlers. Check out the quixotic outdoor bar made from a trio of shipping containers (it folds into itself come ...