The Chicago City Guide

The multi-interested cocktail star has too many ideas, which would be a problem except that the Chicago Athletic Association Hotel hired him to develop four different bars in one place. He explains them here, but ask him yourself (look for the now-famous gray beard).

The tattoo artist, loved for his calm approach, is known for his painterly black and white designs (many of which he test drives on his left “practice” leg—ask to see it.)

He uses his photography skills to celebrate “the fattest most dope views” of outdoor art in Chicago, so his feed functions as a graffiti guide mixed with foodie recommendations.

An inside look at life as the Joffrey Ballet’s lead dancer includes beautiful and sometimes painful snaps from the non-stop world.

The bicycle shop-slash-general store, founded last year by two New York expats, has become a warm, cozy community hub favored by artists, creatives and their adorably dressed children.

Everyone is getting drinks with Hillary, the ultimate extrovert who co-founded A Drink With: a web series of casual one-on-one conversations with influencers, artists, entrepreneurs redefining their worlds, from Richard Branson to Megan Mullally.

Shannon Jamar Eaton Sangster (full name) is a DJ, poet, designer and a nightlife mainstay, which means his geotags are where you want to be.

Chase works in creative strategy at Tumblr, but he could moonlight teaching tourists where to go to take the best photos of the city.

In photographer Molly Miller’s hands, Chicago looks like it’s awash in the softest sunrise/sunset light 24/7, but you really need to look at the photos together to appreciate the beautiful consistency.

His soaring views will have you googling “Chicago helicopter rides.”

The Chicago native built an empire by responding to what the locals seem to love (classic American food) and elevating the experience. Luckily, Eater ranked all of them, right here, and on his feed, Kahan pulls back the curtain on how his kitchens run (that’s his chef @cosmogoss).

The waterfront hotel got a breathtaking, restrained makeover a few years ago, but locals still love grabbing a drink at the bar, or the buzzy Pump Room.

Expert-in-all-things-cool Cody Hudson’s bright, abstract art has been featured in galleries and on buildings all around the world—and as the creative director of Struggle Inc, his restaurant projects (like @parsonschi and @thankyoutakeout) are as stylish as they are delicious.

The outspoken foodie—and James Beard award winner—has tasted almost every pizza in the city and remains one of the last independent food critics, through The Sunday Tribune .

The most compelling case for moving to Chicago and raising a very adorable family, c/o this photographer’s epicurean tastes.

It’s on nearly every “classic Chicago dining spot” list for a few reasons: it’s one of the last drive-ins left, and the hot dogs seem to get better every year without relying on fancy marketing or foodie frills.