A Creative Entrepreneur's Guide to Chicago Essentials

Photos by Sam Grant


With an encyclopedic knowledge of the city’s see-and-be-seen hotspots chronicled on an Instagram feed of more than 100,000 followers, you’d be forgiven for mistaking Nathan Michael as a lifelong Chicagoan.That’s actually not the case at all. “I had no idea what Chicago was about,” says the Texas transplant of moving here nearly a decade ago. “I didn’t even know it was the third-largest city in America.”

No sweat: the Fort Worth native quickly flourished, racking up creative cred as a freelance content creator for a slew of buzzy brands following the design stint that originally brought him to the Midwest. In 2014, Michael ventured into the business world as co-founder of Popular Pays, a platform serving as a marketplace to link creators with big-name brands. Building on his momentum, the Wicker Park denizen left the venture and, in January 2016, launched Low Res Studio, a boutique production studio and event space operating out of a sprawling West Town space so exactingly curated that it feels straight out of a movie studio lot.

And still, there’s an incubative ethos to the 34-year-old’s business. “We try to teach that creativity is for everyone, and like a muscle, the more you use it, it grows.” It’s not lip service. In addition to hosting regular events where intrepid minds can congregate, Michael and Co. host an educational podcast, aptly titled The Creative Muscle, with past guests including author Seth Godin and acclaimed ice cream impresario Jeni Britton Bauer.

Small surprise, then, that a part-time podcast host can wax quixotic on everything Chicago. Below, the authority on all things in-the-know dishes on where to unwind and indulge in the Windy City.

The Right Stuff

Dove’s Luncheonette is probably one of my all-time favorite restaurants. It hits on all the senses. Not only is it incredibly thoughtful and delicious food, but there’s just an aesthetic that takes you back to the feeling of what a restaurant, I think, was supposed to be—there’s this communal element to it, but it’s also just really charming and simply designed in way that takes you back.”


His Cup of Tea

(Photo: Tara White)

Sawada is great. From a matcha perspective, it’s like candy, it’s so delicious. I love Sawada Matcha and Sawada Coffee. They’re excellent.”


Texan-Approved BBQ

Green Street Smoked Meats is what the Texan in me wishes I could eat everyday, but knows it’s not good for me. I love their ribs and their brisket. I feel like what Brendan Sodikoff did at Green Street is better than what most people have done in Texas barbeque.”

Pilsen Pick

HaiSous is probably my favorite restaurant right now. It’s a Vietnamese restaurant in Pilsen that has food you wish you could cook yourself, but makes you want to go out to eat….The flavor profile of his food is just explosive in your mouth.”

Back to the Basics

Sportsman’s Club is a place that serves simple drinks really, really well. They’re affordable and delicious, and I feel like they have some of the best cocktails in the city, if you like classic cocktails….The thing I love is the thing that they’re known for best: their Sportsman’s cocktail. They make their own Amaro, which is incredibly delicious. The patio in the summer is prime.”

Going Green

Garfield Park Conservatory is one of the coolest experiences that Chicago has to offer and it’s free. It’s just one of those places that I want to go back to week after week, because it reconnects you with nature, and it’s so inspiring to see how many incredible plants there are in the world, not only just in the Conservatory.”

Al Fresco Entertainment

“The summer concerts at Millennium Park are what make this city come alive….It’s just the most amazing view of Chicago. I like it because it makes you feel small, but in a good way. It surrounds you with the city’s greatness.”

Pay Homage

“Frank Lloyd Wright was not only one of my favorite designers, but an icon in American architecture. It’s cool to think that he spent so much time in Chicago, and the fact that his home office is a stone’s throw away [in Oak Park] is really cool. His home office is impeccably designed and just makes you want to live life that way.”

The Artful Life

“Going to The MCA in some ways makes me feel like I’m doing sh*tty work, you know? It grounds you in the fact that there’s people doing amazing things out there, because they care about it and they want to create good for the world.”

(Photo: Soho House Chicago)

Go West (Loop)

Soho House is very dreamy. It’s a place where, if you want to get inspired, and you want be in an environment and feel like you’re in another world, it transports you…The Allis is a really great brunch space. It’s very transportive in the sense that it feels European. It’s a great place for a small, intimate one-person coffee or a group party.”

What’s Old is New

“The Chicago Athletic Association is rooted in Chicago history: it’s an old boy’s club that got transported into a beautiful hotel. It was designed by one of my favorite designers, Roman and Williams; that place, I think, is the most beautiful hotel in Chicago, by far.”


Freehand is great if you’re traveling with a group of people and you want to kind of just party in the city cheap….The Freehand is, again, designed by Roman and Williams; they figured out how to do the hostel-style hotel really well.”

Gold Coast Go-To

The Thompson has been one of my personal favorite places to do a staycation at. They have the vibes of the room down….The fact that Nico Osteria is downstairs and you can have an amazing dinner is well worth it.

Interior Upgrade

Scout is my all-time favorite shop in Chicago. Larry [Vodak] is an amazing owner; he’s really whimsical, offbeat, but he is so passionate about design and furniture, that you can’t help but feel his contagious spirit. He just gets you excited about wanting to create a beautiful home.”

On the Nose

Le Labo is what I used to call my best-kept secret, but most people are hearing about it more and more each day. If you like fragrances as much as I do, which would be hard to beat, you’ll never want to shop for a fragrance anywhere else.”

Read All about It

Quimby’s is another Chicago staple. It’s been on Milwaukee [Ave.] for over twenty years. It’s a magazine and bookstore that features mainly independent writers and publishers, and is just a store I could lock myself in for hours and peruse and buy stuff every week.”

FROM LEFT TO RIGHT: Slim Washed Western Denim Shirt, Homage Chicago Bulls Graphic Tee, Skinny Black Stretch Jeans

Produced on location by Stephen Ostrowski.