5 Things Entrepreneurs Need To Do In Chicago This Weekend

A couple weeks ago, I headed back to Chicago for the weekend to catch up with old friends and make some new ones. As we were talking over lunch, I realized that there's so much about this city that I love. I get asked all too often what my favorite Chicago activities are, so here's my definitive list for you. 


Eat at Small Cheval

Small Cheval is quite possibly the best burger joint in the city (and trust me...I've been to most of them). Their locations (three across the city) serve a stripped down menu of the essentials - cheeseburgers, hamburgers, and fries. That's it. It's one of the first places I take guests I bring to the city - especially because Small Cheval is in the same restaurant family as the famed Au Cheval, as well as Green Street Smoked Meats, Sawada Coffee, and a dozen or so others.


Visit Koval Distillery

If you've known me for any amount of time, you know that I could write a love note to Koval for all that they've given me. I'm a massive fan of their spirits (that are organic, kosher, and mostly gluten free). KOVAL was Chicago's first distillery since the mid-1800s.

The name KOVAL means "blacksmith," in numerous Eastern European languages, but the word in Yiddish also refers to a "black sheep" or someone who forges ahead or does something new or out of the ordinary, so naturally I fell in love with their slightly-anarchist roots as well.

All of KOVAL's whiskies are "single barrel" expressions and aged in 30 gallon charred barrels. This insures that the distillate, made up solely of the heart cut (which is unique among whiskey distillers), is able to develop its flavor with the purest grain notes. 

KOVAL does daily tours, you can book them here!


Stay at The Gray Hotel

There's nothing I love more than a beautiful hotel room and Kimpton never fails me. The Gray is Kimpton's newest offering in Chicago, a stunning and historic home away from home. The hotel is in the historic New York Life Insurance Building (originally built in 1894). The hotel is actually named for the Georgia Gray marble found throughout the building. 

I quickly fell in love with Vol. 39, this bar that feels like it's right out of a law library. It's cozy and the perfect place for sipping a glass of whiskey. If you're looking for something a little more adventurous, check out Boleo, the top-of-the hotel bar and lounge with a retractable roof! 

I snagged a couple photos of my favorite spots throughout the hotel - the beautiful blue doors, the art found throughout, and the lobby being some of the most unique! 



See western avenue.

Did you know that Chicago's Western Avenue is the world's longest continuous street, at 23.5 miles? There's so much to see on Western Ave - 64 bars, the South Side Irish Parade, and plenty of sightseeing. Take some time to walk the street when you're visiting the city!

Of course, I've taken friends on many of these adventures and even checked out a few extras - here are some photos from a recent entrepreneur gathering I hosted in the city.