Forgive me friends, it has been a few months but I am finally getting around to sharing the details of my trip to Chicago!  I attended college in Missouri so as you can imagine many of my classmates came from neighboring Illinois.  As such, I have made quite a few visits over the years and have some great friends who call Chicago home.  This spring I spent the weekend in Chicago with my best friend and we ate at ALL the good places in Chicago.  While this post is late, it still includes so many great places that I think you all will enjoy during a Weekend in Chicago.

Truth Italian Restaurant

Stemless Champagne glass with layer of red strawberry puree at the bottom, champagne and a strawberry garnish

On my first day in town we got up early to visit Truth Italian Restaurant for a weekday breakfast/brunch.  This Italian Restaurant is owned by a black woman, which I of course loved.  My friend shared that one of the chefs behind Batter and Berries helped develop the brunch menu at Truth, bringing their famous french toast to this location.  There french toast was amazing as were their unique mimosas.

White plate with three pieces of french toast topped with fruit

Cooper’s Hawk

Cooper's Hawk Wine Glass

I loved the concept of Cooper’s Hawk, a winery/restaurant with locations all around Chicago.  With a membership, you get monthly access to the tasting room plus bottles to go.  My friend just happened to have a few passes for the month during my visit, so we enjoyed a tasting and grabbed some bottles to go.  Definitely left a little tipsy, but I enjoyed it.


White bowl with macaroni and cheese in the foreground and white bowl with greens in the background


White Plate with Fried Chicken

My friend has known the owner of Soule, Bridgette, since college and told me about the restaurant for years.  As much as we talk about black owned restaurants, we should also note that the rarity of restaurants owned by black women!  For these reasons, I was excited to try Soule during my visit.  Described as a “boutique restaurant” on Chicago’s westside, Soule offers guests traditional soul food items and a few things like chicken spaghetti that you may not see other places.   We kept it simple during our visit and went with the fried chicken and mac & cheese.  Highly recommend!

Brown Sugar Bakery

Black hand holding a vanilla cupcake with white wrapper and pink frosting in foreground and Brown Sugar Bakery sign in the background

Right before my visit to Chicago, Vice President Kamala Harris visited and stopped by Brown Sugar Bakery.  So I course added it to my visit list.  On my way out, we even chatted with the owner who was sitting outside visiting with friends.  She was very nice and I loved hearing the stories behind some of her most popular items like the Obama Cake.   Be sure to stop by for a good sweet treat.

Layered cake with chocolate layer, yellow layer, red velvet layer, and another yellow later.  White icing.


Margarita with tahin straw and slice of lime

It should be no surprise that a brunch was on the agenda.  My friend saw videos of Azul on TikTok and thought it was the fun brunch vibe we were looking for.   Located on the Chicago River, Azul offers Latin dishes and a fun party atmosphere.  Now, this Latin restaurant did not bring you the customary free chips and dip, but they do bring each guest a small cocktail to get started.  For food, we enjoyed the lobster empanadas and tacos.  The highlight there of course are the drinks including their patron drink towers.

Lobster Empanada

Blue plate with two steak tacos and a cup of salsa

Lou Malnati’s

Overhead photo of a Lou Malnati's Deep Dish Pizza

Did you visit Chicago if you do not eat pizza?  There are tons of options for Chicago style pizza, but I have always preferred Lou Malnati’s.  I stopped by their location near Midway on my way to the airport for a personal sized pizza and salad.  Delicious!

Deep Dish Pizza

Virtue Restaurant

So when I travel, I am looking for two things and honestly these two categories rarely meet.  Really cool perhaps fine dining experiences and also black owned restaurants.  Like Lucille’s or Davis Street back home, Virtue Restaurant was a combo of both.  We visited in the evening so I didn’t get any pictures because it was too dark.   On your visit, be sure to order one (or two) of their amazing cocktails, the mac and cheese and cornbread.

The Takeaway


During my visit there are beautiful tulips along Michigan Avenue.

Whew! We ate A LOT during a weekend.  There are few cities that have the level of food scene that I enjoy in Houston, but Chicago is definitely up there including their variety of black owned businesses.  Another quick note, many of these restaurants are very popular in Chicago, so we made a point to make reservations for our visits, so I would recommend the same.