Nicknamed the Windy City—which, contrary to popular belief, is not because of windy weather—Chicago is a destination worthy of everyone’s travel list. A diverse city that is home to bustling neighborhoods and vibrant communities, the “Second City” proves itself to be a rich tapestry of languages, traditions, and cuisines from around the world.
While most Chicago-bound travelers know to check out the Magnificent Mile (the Windy City’s answer to New York’s 5th Avenue) or the Willis Tower (formerly known as the Sears Tower), there is a slew of BIPOC and women-owned businesses worth supporting while in town. From charming bookstores to artisan boutiques and authentic Spanish churros to modern Southern cuisine—here’s how to visit Chicago in a way that supports its diverse and entrepreneurial communities.
The Book Cellar
Now, color us biased, but the Book Cellar is truly one of Chicago’s literary gems. This independent, woman-owned business was founded by Suzy Takacs in 2004 and has since become a pillar in the Lincoln Square neighborhood. Not only is the Book Cellar a wonderful bookstore, but it doubles as a wine bar and an event space that regularly hosts local and visiting authors, including Unearth Women’s founder Nikki Vargas, who held an event at this beloved shop during the book tour for her memoir, Call You When I Land.
The Silver Room
Founded by Eric Williams back in 1997, The Silver Room is a Black-owned shop that is so much more than a store. With a mission to create a global community through art and culture, this Hyde Park institution (with BIPOC women at the helm as creative director, buyer, store manager, and shipping and receiving manager) is not only known for its diverse selection of jewelry, art, and accessories but is also a community space regularly hosting events. From poetry nights to album release parties to pop-ups to open mics, this is one of those neighborhood gems that perfectly reflect the talent, diversity, and love of its residents.
Felt
According to its website, “Creative partners Catherine Dunton & Holly Grannan established FELT after a chance meeting on a Saturday at Satine Boutique in Venice, California. Kat sold Holly a pair of purple Jenni Kane D’Orsay flats,” and the rest, as they say, was history. Today, FELT is a trendsetter in the Logan Square neighborhood that pairs established clothing designers with up-and-coming ones in its upscale boutique store. What sets FELT apart is its individualized approach to styling for each of its clients.
Chicago Women’s History Center
While it’s important to support BIPOC and women-founded businesses whenever you travel, it’s equally important to learn about the history of the destination you’re visiting. Enter the Chicago Women’s History Center, a non-profit organization dedicated to documenting, preserving, and sharing resources for the study of Chicago women’s history. The Chicago Women’s History Center is an important organization that is worth supporting—whether you choose to volunteer, purchase an item from its store, or plan to join one of its upcoming events.
Squasht Boutique
Owned and founded by Lesley Timpe, Squasht Boutique offers handmade clothing, accessories, and jewelry with a vintage-inspired aesthetic in Chicago’s Ukrainian Village. This independent shop offers a colorful and eclectic mix of clothing, ranging from jumpsuits to HomeGoods.
Urban Oasis Spa
Escape the hustle and bustle of city life at Urban Oasis Spa, owned by spa maven Jessica Thompson since its founding in 1992. With indulgent treatments and a serene ambiance, this spa offers a tranquil retreat for rejuvenation and relaxation.
Renegade Handmade
Co-owned by Sue Daly and Erin White, Renegade Handmade features handmade goods from independent designers and artists in Wicker Park. Beyond being a destination for unique finds, Renegade (much like other beloved businesses on this list) doubles as a community space for its neighborhood. “All Renegade events and endeavors are produced, juried, and curated in-house by our small yet mighty team,” reads its website. “We’re a thoughtful group of artists and doers that are inspired to build, cultivate, and foster creative community.”
Xurro
Owned by Chef Ximena and Edwin, Xurro is a popular churro shop in Chicago, known for its delicious and freshly made churros. They offer a variety of churro options, including classic plain churros, filled churros with different fillings like chocolate, strawberry, and cream cheese, and churro sundaes with ice cream and toppings. Xurro has several locations throughout Chicago, including in Logan Square, Northcenter, and Pilsen. They are known for their friendly service and affordable prices, making them a great spot for a sweet treat.
Bang Bang Pie & Biscuits
Co-owned by pastry chef Megan Miller, Bang Bang Pie & Biscuits is a rustic bakery in Chicago’s Logan Square neighborhood, known for its delicious and homemade sweet and savory pies and biscuits. The bakery has a rotating menu, so there’s always something new to try. Some popular items include the cherry pie, peach pie, chocolate chip pie, and cheddar cheese biscuit.
The Sassy Spoon
Owned by Chef Sarah Smith, The Sassy Spoon is a popular restaurant in Chicago known for its delicious Cuban-inspired cuisine. They offer a variety of dishes, including sandwiches, soups, salads, and desserts. Some of their most popular items include the Cuban sandwich, the ropa vieja, and the tres leches cake.
Virtue Restaurant
Owned by Chef Ericka L. Durham, Virtue Restaurant is a highly acclaimed Southern American restaurant located in Chicago’s Hyde Park neighborhood. It is known for its innovative and flavorful dishes that showcase the best of Southern cuisine, using fresh, high-quality ingredients and traditional cooking techniques. Today, the restaurant is led by Chef Donald Welch, who was awarded the James Beard Foundation Award for “Best Chef: Great Lakes” in 2023.
Soulé Chicago
Owned by Chef Bridgette and Leroy, Soulé Chicago is renowned for its authentic New Orleans-inspired dishes. Its flavorful Cajun and Creole cuisine has garnered rave reviews, establishing it as a culinary gem in the Chatham neighborhood.
The Publishing House Bed and Breakfast
Owned by Sue Kim-Drohomyrecky, The Publishing House Bed and Breakfast is a hip, industrial-style boutique B&B in a former publishing house featuring eclectic rooms & a bar. This boutique bed and breakfast offers a charming blend of historic architecture and modern amenities in the West Loop neighborhood.
Hotel Lincoln
Owned by Sheila King, the 4-star Hotel Lincoln offers a unique blend of vintage charm and contemporary comfort in the heart of Lincoln Park. With stunning views of Lake Michigan and the Chicago skyline, it’s a favorite among travelers seeking a memorable stay.
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