When asked to write a blog about innovative brick & mortar businesses in Chicago, my mind instantly turned into a bizarre montage of Michael Jordan dunking a deep-dish pizza at Wrigley Field.

Clearly, I was overwhelmed with the task at hand because there is so much to be said about the soul and spirit of the Windy City. I flashed back to reality and quickly realized that Chicago’s small business sector is much like the city itself; it stands out. It’s a metropolis of culture and entertainment among wheat fields and factories in Illinois.

Here are 4 shops that are uniquely Chicago and standing out in a big way.


1. Stan’s Donuts & Coffee

box of assorted donuts

Known for inventive flavors and a sprinkle of personality, the atmosphere at Stan’s Donuts & Coffee cannot be matched.

Customers can choose from over 20 flavors of pastries ranging from sweet staples like Chocolate Glazed to the new Captain Crunch. Stan’s didn’t originate in Chicago, but after 50+ years of success in Los Angeles, owner Stan Berman decided it was time to open up shop in Chicago to bring a taste of Cali to the Midwest masses, and boy are they happy he did! Hot chocolate served with mini donuts on top, Nutella Pockets (think gourmet handmade dessert style Hot-Pocket), and freshly brewed java all day make for the perfect companion in that crazy Chicago cold!


2. Milt’s BBQ for the Perplexed

BBQ sandwich and coleslaw

When you hear the word “Kosher”, I am sure “BBQ” is not the next word that comes to mind.

In addition to a slew of BBQ mainstays, Milt’s features several vegetarian options like vegetarian chili, tofu dogs, and even veggie chili fries! Opened to nourish the mind and the body, Milt’s dining room also features captivating speakers from around the world to educate and entertain in the realm of politics, history, comedy, religion, and more. Just when Milt and his crew couldn’t get any cooler, he announced that 100% of his profits will go to charity. Milt’s BBQ is flippin’ the script on Kosher cuisine by serving up some of the most mouthwatering meat and crave-able conversation for a good cause!



retail store in Chicago

Chokers, Pokemon, and Full House have all made major comebacks this year, so shouldn’t someone capitalize on that? KOKOROKOKO (try saying that 5 times fast) is your one-stop shop for all things 90’s. Not just for themed parties and Halloween, KOKO is your year-round place for scrunchies, fanny packs, and high-tops.  The owners have carefully curated the perfect mix of nostalgia and high fashion on Milwaukee Ave, one of Chicago’s busiest shopping streets. Center stage in Chicago’s hip Wicker Park neighborhood, this funky find is one of many small businesses that are the backbone of trends and style in Illinois.


4. The Public Barber

barbershop haircuts

Located in the Uptown neighborhood, The Public Barber is a community-based barber-shop that is giving out a lot more than just haircuts. Built on the principles of human connection, TPB focuses on the ambiance, conversation, and connection as much as they focus on the cuts themselves. You never know when you pop in there which local artists, performers, and musicians will be there to entertain the clientele. With services on the menu like scalp treatments and hot lather shaves, the barbers at The Public Barber have become somewhat of grooming gods in Chicago. The Public Barber is bringing soul back into service.


Editor Note: References made to businesses/companies in this post are not meant to convey endorsement by Rubicon of those companies in any way.