If you’ve never been to Chicago, a.k.a. Chi-Town, The Windy City, and The White City among other nicknames, consider adding it to your list. For generations, it has been shaped by Black people, starting with the “the Father of Chicago,” Jean Baptiste Pointe DuSable, who arrived there from Haiti in the 1770s. In 2021, Lake Shore Drive was renamed in honor of DuSable’s work as a successful tradesman and entrepreneur. What better way to honor his legacy than supporting Black-owned Chicago?

According to Choose Chicago, “The Great Migration brought hundreds of thousands of African-American migrants to Chicago,” and they were responsible for infusing the city with jazz and blues music. Today, there are a number of clubs offering live music in these genres. The city also witnessed the election of the nation’s first Black-president, Barack Obama, who issued his victory speech in Grant Park in 2008.

Chicago is exciting, fast-paced, and international, offering plenty in the way of shopping, restaurants, and culture throughout the year. And you’d be remiss not to try the deep-dish pizza at least once, though some New Yorkers would call it tomato pie since it can’t be folded. Whatever name you choose, it’s delicious.

Here are some Black-owned Chicago businesses to patronize during your 48-hour stay in The Windy City.

Day 1 - Morning


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Welcome Inn Manor is expected to eventually re-open after an extensive renovation process, and will make a great place to stay during your trip. Visit the website for more details.

This charming, vintage home is the only bed and breakfast of its kind in the city, and there are six comfortable rooms available for rent. Communal spaces such as the terrace and the living rooms are good places to mingle with other guests and learn about some sites in the city that are off the beaten path.  A full breakfast is offered at set hours.

If you’d rather have breakfast elsewhere, visit Batter and Berries. The founders, Dr. Tanya Richardson and Craig Richardson, along with Chef Ken Polk, aim “to provide delicious food in a fun and uplifting atmosphere.”

There are some delicious options for lunch and dinner too, like the lemon dill salmon and the grilled lambchop with red wine and rosemary.

Day 1 - Afternoon

Are you an avid reader looking to support The Culture? Head over to Semicolon Bookstore, which is proudly Black, woman, and LGBT+ owned.

Their aim is to not only sell books, but to tackle literacy issues which disproportionately impact Black communities.

To that end, they created a hashtag on Instagram, #NationalBlackLiteracyDay.

Forty Acres Fresh Market was created to make produce affordable. It was founded by Liz Abunaw.

According to the website, the organization “operates as a mobile grocery store and hosts pop-up markets in underserved communities.” Check out their market schedule here.

Now, perhaps more than ever, the stigma around mental health should be dissolved, especially in the Black community.

Coffee, Hip Hop and Mental Health was designed to shed light on this very subject. Founder and musician Christopher LeMark created the organization after fighting his own battle with depression and PTSD.

As highlighted by Time Out, “by working with licensed therapists to create safe, coffeehouse-style spaces, this organization has helped communities normalize therapy and have honest conversations around mental health.”

Looking to cater to your sweet tooth? Head to B & B Candy And Ice Cream for both of those and more. There’s one location on South Racine and another set to open E. 63rd Street.

Day 1 - Evening

It’s time for dinner! Head over to Luella’s Southern Kitchen, founded by Chef Darnell Reed. Even though the cuisine is Southern-inspired, Reed’s experience as a culinary expert is shaped by his international travels. The restaurant is named after his great-grandmother.

Grab a late-night cocktail at M Lounge, which advertises itself as “the best lounge in Chicago’s South Loop.” Proof of vaccination and corresponding identification are required.

Day 2 - Morning

Before starting your second day of patronizing Black excellence, go for a walk or ride a bike parallel to Lake Michigan.

Have you ever wanted to try one of those sip and paint events? Pearl Paint and Sip, founded by Carl Nicolas, helps you tap into your creativity.

This hip, stylish venue is located in Wicker Park, and even if you can’t draw a straight line with a ruler, you’ll have a great time. Please note it’s BYOB.

Day 2 - Afternoon


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Looking to get a good sweat going? Head to 360 Mind Body Soul, a fitness studio founded by Ashanti Johnson. Classes offered include boot camp, spin, HIIT (high intensity interval training) and Zumba.

Want to take in some Black art and history? Go to Gallery Guichard or The DuSable Museum of African American History.

The latter is the oldest, independent African-American museum in the country. It not only houses countless paintings, sculptures, and other works of art, it also hosts films and events.

Check out the schedule here.

Day 2 - Evening


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If you’re looking for a place to dine or have a snack with patio seating, Chicago has you covered.

The Delta takes its cue from the Mississippi Delta region. If you go earlier in the day, partake in their delicious Sunday brunch with bottomless mimosas out on the enclosed patio. It’s also known for its tamales and cocktails.

In Bronzeville, there’s Truth Italian Restaurant, owned by Peytyn Willborn, who puts her own twist on Italian delicacies.

Try the jerk chicken alfredo omelet or, for something with no Italian roots, check out the tacos, French toast, and catfish.

Grab dessert at Ina Mae Tavern, serving slushies in Wicker Park, with New Orleans flavor.

Vegan or vegetarian? Check out Majani or Can’t Believe It’s Not Meat.