Chicago is a sprawling city with plenty of large and small businesses to entertain visitors and residents alike. Smaller businesses provide a unique and more personalized experience that may be more enjoyable than shopping with a bigger company. If you want to support smaller businesses, here are a few that you can check out the next time you’re out and about shopping in this incredible and diverse city.

Monday Coffee Co.

Chicago sign
Image via Flickr by kevin dooley Licensed CC BY 2.0

Founded by Amanda Christine Hart and Felton Kizer, Monday Coffee Co. is a concept they developed while working their daily jobs. They quickly found their coffee business growing and becoming a full-time gig. They focus on small-batch brewing and bottling, preferring to provide quality over quantity. Using beans picked and roasted in Michigan, this Black-owned business creates a great Midwestern coffee and provides a relaxing and comfortable experience that allows customers to connect with each other. You can buy online or visit the shop, where the owners still spend much of their time working the counter.

Luvsick Plus

Luvsick Plus is a shop dedicated to plus-size fashion that repurposes vintage clothes in unique and innovative ways. Their styles accentuate a plus-sized woman’s natural beauty and come in sizes 12 to 24. Started by Brittney Riordan when she struggled to find clothes that fit her properly, LuvSick Plus is perfect for the fashionable plus-sized woman in Chicago who wants attractive vintage clothes to fit her chic sense of style. Visit the shop in person or order online to get the fashionable looks you want for your closet.

Semicolon Bookstore

Semicolon Bookstore is Chicago’s largest shop owned by a Black woman. Since opening up in 2019 during her cancer treatments, Danielle Mullen has spread her loving of reading to many people across the city. She also started Paren(t)hesis, a nonprofit pop-up used bookstore that helps support literacy causes throughout the Chicago area. You can stop in to shop for their multiple book options, buy online, and join their mailing club for updates. Even better, Semicolon Bookstore supports marginalized artists by providing a gallery where they can display their latest and greatest works.

The Lotus Den

The Lotus Den is a spiritual-oriented shop that focuses on affordable gear for practitioners. Their shop includes things like hand-picked crystals and jewelry, high-quality books, and even Reiki sessions. You can speak with a professional about your own spiritual journey, including any troubles you’ve encountered along the way. This store also holds many events, including talks with spirituality experts and guided meditation sessions.  The Lotus Den allows you to purchase items in-store and offers online sessions for those who prefer virtual appointments.


Chicago children all around the city deserve a special shop that focuses only on their needs. Kido is a Black-owned shop that provides a variety of kid-friendly products, including eco-friendly clothing, toys, puzzles, baby gifts, and books. You can sort through their belongings by age and look for sales that save you money. Kido specializes in products that carry positive, empowering messages for children of diverse backgrounds. They also provide a reading event called Story Times to provide a space for families to spend time together. Visit their shop in person or online to see their wide range of products.

G.V. Jewelry

Are you looking for high-quality jewelry that is custom-fit for your needs? G.V. Jewelry may be the right place for you. This family-owned and operated shop prioritizes inclusivity. Current owner and designer, Julio Velazquez, son of the original founder, works hard to provide personalized pieces and hands-on care for his clients. He creates designs himself based on client needs and completes the process himself all the way to the finished result. If you want to purchase his high-quality jewelry, check out G.V. Jewelry’s website or stop by the shop.

Los Naturales

Chicago offers a fascinating variety of wines with multiple styles and tastes. Los Naturales is a wine-selling company that helps newcomers find their wine-of-choice, providing customers with to-go bottles and bar specials. When visiting, you can learn all about winemaking, discover great deals, meet new friends, and stock up on your favorite selections. While you’re here, you can also relax in the tasting room and listen to some calming music. While only open on Saturday and Sunday, Los Naturales provides a great weekend destination for the wine aficionado who wants to support a smaller business in the local area.

Wish Me Luck Tattoo

As Chicago’s first Black, Queer, and Trans-owned tattoo shop, Wish Me Luck Tattoo is dedicated to uplifting the community by providing high-quality artwork in the form of tattoos. Wish Me Luck Tattoo is by-appointment-only, so don’t forget to visit the website to book a slot and view your pricing options. After scheduling an appointment, you can have a tattoo designed by expert artists, each specializing in a different art style. Don’t forget to shop on their website for hats, sweaters, and T-shirts.

Plant Salon

Chicago resident Nika Vaughn opened Plant Salon to combine her two big loves: plants and the beauty industry. This beautiful shop provides many handmade beauty products, including lip balm and beard oil. You can also pick up goods for the home, including bath salts, candles, and mugs. Select from multiple plant options to find one that fits easily into your home, providing a natural feel to any place of residence. Visitors comment regularly on the store’s friendly nature, as Vaughn still regularly works the shop and provides expert advice to customers.

So, there you have it. We’ve listed multiple small businesses that operate in and around Chicago. Did you enjoy our list? Did we miss a business that you feel deserves more recognition? Contact us today to let us know and we’ll be happy to update our list with your suggestion. Our expert team at American Auto Insurance is proud to serve Chicago residents and help you find what you need.


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