Best Eats in Chicago: Restaurants & Foodie Experiences with Shannon Boland

Shannon Boland (Photo: Ten Photos)

Shannon Boland is ebullient, with bouncy coffee-colored curls to match. It’s the perfect personality trait for her job as head Navigator Concierge at the Renaissance Blackstone Chicago Hotel. Like most of us, Boland has a thing for good food. The actor and St. Louis transplant researches Chicago restaurants three times a week. Here, she delivers the scoop on Chicago foodie faves.

What foods should every Chicago visitor try?

When I first moved to Chicago seven years ago, I was sent to Portillo’s first. I got the Chicago dog, cheese fries and that amazing chocolate cake. It was everything I expected. Giordano’s was next. I’m embarrassed to say it, but I’m not a deep dish person. It’s part of the Chicago experience but I prefer Pizano’s for thin crust. People always look for hot dogs and pizza but this is a steak town as well. This is a meat and potatoes place with a steakhouse on every corner. I recommend Gene & Georgetti’s because it’s got that old Chicago feel. You feel like Lucky Luciano will sit down right next to you.

What are some unexpected foodie experiences?

I would say the resurgence of the speakeasy is pretty unexpected; every Chicago restaurant has an underground tavern now. At The Aviary, the things they’re doing are insane. They pair small bites with experimental cocktails. I had a cocktail called “In the Rock” and it arrived as a block of ice, no liquid. I looked at the waitress and she smiled and took out a slingshot. She shattered the sphere of ice and out poured the drink. There’s The Franklin Room, an underground restaurant under Franklin Street, that serves 100 different kinds of whiskey. I’m a whiskey girl so I love that they actually have whiskey lockers. You join the club, buy a bottle of whiskey and every time you go, they’ll serve you your bottle from your locker.

Are there neighborhoods that travelers should check out for good food?

Chicago is a city of neighborhoods so neighborhoods always come into play. I send guests to Wicker Park for tacos at Big Star or Penny’s Noodles, when they want something more local and not so touristy.

Since it’s close to downtown Chicago, I also send a lot of people to Chinatown to try Phoenix, Triple Crown or Three Happiness and they can also go shopping. Pilsen, Andersonville and Logan Square all have great neighborhood eats. I send people to my neighborhood of Uptown, to the Green Mill and Demera Ethiopian Restaurant across the street.

Any tips for getting into popular restaurants?

Using your hotel concierge is always a good thing. We talk to restaurant managers enough so that sometimes we can facilitate things. But it’s a good rule to always book early, especially for weekends. Another trick is to arrive when the restaurant opens. At Girl & the Goat, if you go when it opens at 4:30, you can order the entire menu in the lounge. You’ll sit at a communal table and have an experience with travelers from all over the world.