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Thompson Hotels Influencers Chicago X Deanna Leess


The Sustainable Food Advocate

Deanna Leess lives and breathes Chicago’s foodie culture. Just check out her Instagram account, where she posts pictures of the best sandwiches, sweets, and the fancier meals she consumes.

When she’s not managing a hip Chicago restaurant, Deanna volunteers at The Plant, a fully sustainable food production facility the South Loop. The Plant produces the only farmers market in Chicago with small batch coffee, gourmet mushrooms, naturally leavened bread, and more items being sold in the same space they’re produced.

Deanna told us what she loves about Chicago’s food scene and how to break in.

What attracted you to the Chicago restaurant scene?

First of all, Chicago is a straight-up foodie town. Chefs love what they do and share that love with the city, showing off their creativity. There is always something new to try, somewhere that everyone is talking about. Second of all, the city has a rich history in food production. Walking along the West Loop, you feel as though you’re going back in time—all of the old meatpacking warehouses surround you. Some are still producing. Subsequently, no city does meat like Chicago. My hunt for the Chicago’s best burger is ongoing and especially enjoyable.

When you get off work, where in Chicago do you like to visit?

In the summer, I love any bar with a patio or a rooftop bar. In the wintertime, you can find me at Watershed, an underground bar full of 60s feels and a drink list to match. For a swanky, boozy evening, I’ll head to the Broken Shaker. J. Parker has delicious craft cocktails, and its location north of downtown keeps it less touristy.

What’s the best part of summer in Chicago?

The energy. Everyone takes advantage of what the city has to offer. Just walking along the Lakefront Trail, with city views on one side and the beach on the other, I’m reminded of all the city has to offer.

How did you get into working in restaurants, and what’s your advice for people trying to break in?

I’ve loved food and restaurants since I was a little kid, and I majored in Hospitality Management at The Ohio State University. I started working in restaurants when I was in high school, as a hostess. I love the feeling of being and working in a restaurant, although at times it’s exhausting and exasperating. I continued to work throughout high school and college. I started a management-training program with Hillstone Restaurant Group before moving to Chicago.

My advice for people trying to break in is to just start getting your hands dirty. Look for restaurant groups or individual restaurants that are passionate about what they do. Be willing to work from the ground up.