Artist Nate Otto Talks Chicago’s Best Pizza, Buildings, Bookshops and More

The Windy City-native shares his go-tos

August 11, 2023 6:16 am
Local Chicago artist Nate Otto in front of mural
Local artist Nate Otto shares his insights on the best-of spots in the city
Nate Otto

You might not know his name, but Chicago residents have probably seen artist Nate Otto’s work painted on indoor and outdoor walls all over Chicago, for businesses ranging from Walgreens to Warby Parker. Here, Otto shares his insight on the best places to go in the city for art, food and more — and why his hometown is a superb place for creatives (read: affordable rent). 

InsideHook: We love a restaurant where only locals go — what’s your favorite?
Otto: Kimski in Bridgeport deserves recognition. They serve delicious Polish / Korean fusion, and they have a great atmosphere.

Where should I go for a big night out on the town?
It depends on whether you’re looking to eat or drink and how much money you want to spend, but in terms of a general area, I think the main drag in Logan Square along Milwaukee Avenue can meet the needs of just about everyone. It’s a really hip and thriving area, and there are a bevy of places to dine and imbibe. 

Best budget eats in town?
I’m really partial to a little-known place on 95th Street called Flippin’ Flavors. They have tremendous sandwiches and are virtually unknown.

Where can I go for the best dessert?
I’m admittedly not a big dessert guy, but I do like ice cream. It’s hard to beat Ohana at Wood and 103rd. As a bonus, there’s a mural I painted on the side of the building. 

Best place for a sunset cocktail?
The sunset in Chicago is great. You won’t see the sun dipping below the horizon, but you will see the sky turn red, orange and pink. The best place to watch a sunset in Chicago is from a boat on the lake where you can see the sun drop behind the skyline. If you don’t have a boat, a friend with a boat or happen to get invited on a boat by a stranger, then you can settle for one of the many beer gardens in the city. Parson’s Chicken and Fish works. 

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Best neighborhood to take a long stroll if I want to get acquainted with the city?
Downtown Chicago is beautiful. Stroll along the river or down Michigan Avenue. I’d say that is a good place to start. The life in the neighborhoods is what really makes the city sing, but it’s easy to forget how majestic downtown is.

Where is the best place to check out public art in Chicago?
I love the Cultural Center. There are a few galleries there, and they show really relevant and interesting work. It’s free and it’s a great building to explore.

What’s your must-go museum in Chicago?
The Art Institute is a world-class museum and always worth a visit. I’ve been there a hundred times and I always find something new. 

Chicago is known for its architecture, and you feature buildings and cityscapes in your work. What Chicago building excites your imagination?
There are so many great buildings in Chicago. Oddly, I’ve always been fascinated by the old Prudential building. Just the fact that it was once the tallest building in town, and it’s now dwarfed by so many of the buildings around it — really sparks my imagination. 

What’s your favorite art gallery?
The local gallery landscape is ever changing. The galleries all used to be in River North, then many popped up in the West Loop and now many reside on Chicago Avenue. I like Carl Hammer because it has largely remained the same for a long time, and I love the work they show. I’ve also met the man Carl Hammer, and he struck me as a true gentleman.

What’s your favorite bookstore?
Myopic Books is an institution in Wicker Park. I also dig Bookie’s in Beverly — it’s a representative of all of the independent bookstores around the city. 

We love getting out into the park in a big city, so which Chicago parks should be on our “don’t miss” list?
There is so much energy and life radiating from Humboldt Park on a summer day. The lagoon is a beautiful setting in particular, and I don’t think people from outside the neighborhood even know it’s there.

Where’s the best place to get Italian beef or a Chicago hot dog?
For Italian beef, I really like Bari Foods on Grand. They are mostly known for their Italian subs, but their Italian beef is also great. When it comes to hot dogs, I suppose I don’t have the palate to discern the difference between many of the hot dogs offered around town with the exact same ingredients, but recently I was up in Deerfield painting a mural and I had a craving for a hot dog. I swung by a place called Josh’s Hot Dogs in Northbrook, and the hot dog I was served was near perfection.

What food does your city do better than anywhere else?
There is a lot of pizza pride in Chicago. Everyone knows about Chicago-style deep dish, but most locals prefer the thin-crust, tavern-style, square-cut pizza. Everyone has their favorite — I think the best I’ve had is at Vito and Nick’s Pizzeria

What’s the best thing you can only do in Chicago?
The best thing you can only do in Chicago is afford the rent while living in a cosmopolitan city that has everything that only the biggest cities have to offer.

Best place to eat a meal or have a beer outside when the weather’s better?
The wait is ridiculous sometimes, but I love Big Star on a nice day. There’s no better way to spend the early evening than at one of those precious outdoor tables at the Wicker Park location.

Finally, what’s the best book to read about the area before someone comes?
I think my favorite Chicago book is Devil in the White City by Erik Larson. It really lays out the history of the development of the lakefront and how Daniel Burnham’s design helped make the city such a beautiful place. 

You can check out Nate Otto’s work on his Instagram and his website.


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