Chicago
Check out my Chicago weekend itinerary as I supported and highlighted locally owned businesses, checked out some popular attractions, took in some arts & culture, and share hotel recommendations.
Choose Chicago hosted this trip, which is the official tourism board for the Windy City.
* denotes the business is Black-owned
Thursday
Breakfast @ Yolk
With 8 locations throughout the Chicago area, this breakfast and lunch spot makes it easy to get your breakfast fix.
Multiple Locations
Dom’s Tip: This is a BYOB establishment.
Happy Hour @ 14 Parish Restaurant & Rhum Bar*
Caribbean fusion restaurant offering over 100 types of Rhum with great music and colorful decor located in Hyde Park.
1644 E 53rd St, Chicago, IL 60615
Dom’s Tip: Order the Hyde Punch and Jerk Catfish.
Hyde Park cocktail
Dinner @ Daisy's Po-Boy and Tavern*
Owned by Chef Erick Williams, is a casual eatery serving authentic New Orleans-style po' boys and Southern favorites, complemented by a selection of cocktails.
5215 S Harper Ave, Chicago, IL 60615
Nightlife @ Moneygun
This Loop bar offers a diverse crowd, great music, and classic cocktails.
660 W Lake St, Chicago, IL 60661
Friday
Breakfast @ Sweet Maple Cafe*
This cafe has been serving Chicagoans hearty breakfast and lunch since 1999. The biscuits are unforgettable and the food will have you considering how you can plan a trip back before your visit is over.
1339 W Taylor St, Chicago, IL 60607
Dom’s Tip: The biscuits are a must and load up your homefries with the additional add ons.
Sightseeing @ Skydeck
Located at was previously known as the Sears Tower and now the Willis Tower on the 103rd floor will have clear views of 4 states.
233 S Wacker Dr, Chicago, IL 60606
Dom’s Tip: There is a food hall located inside the Willis Tower, and is the perfect way to find something for everyone in your group.
Dinner @ Luella’s Southern Kitchen*
Located in Lincoln this counter-service restaurant and named and inspired by the chef’s grandmother, Luella. Here you can find creamy mac n’ cheese, collard greens, chicken gumbo, and more.
4609 N Lincoln Ave, Chicago, IL 60625
Dom’s Tip: This is a BYOB establishment.
Shrimp & Grits
Saturday (Chill Day)
Dinner @ Virtue*
Located in the historical Hyde Park neighborhood this James Beard-nominated Southern American restaurant offers items such as green tomatoes, gumbo, and blackened catfish to name a few.
1462 E 53rd St, Chicago, IL 60615
Dom’s Tip: Make a reservation or if you decide to come as a walk-in get there a couple of minutes prior to opening. Snagging a table at this table and the wait is worth it. Order the gumbo, cornbread, green tomatoes, collards, and Strawberry Fields cocktail, and I PROMISE you won’t be disappointed.
Cornbread & Honey Butter
Drinks @ Punch House
Located at the bottom of a restaurant this bar is perfect for groups and offers its cocktails in a glass, carafe, or punchbowl. This bar offers a diverse crowd and great music.
1227 W 18th St, Chicago, IL 60608
Dom’s Tip: If you are seated at the bar at midnight you get a free shot on the house.
Sunday
Live Music & Dinner @ Tribe*
Known as one of Chicago’s premier venues for live music, offering bottle service, and a Caribbean fusion fare. You are able to walk in but reservations are strongly encouraged. Tribe offers live performances Thursday @ 8pm, Friday @ 7pm, Saturday @ 8pm, and Sunday @ 8pm . After the live set, a featured DJ will start spinning for the remainder of the evening.
1239 W Lake St, Chicago, IL 60607
Dom’s Tip: Make a reservation well in advance to ensure you can secure a table for the live performances.
Jerk Chicken Taquitos
Attractions or Points of Interest
Grant Park which includes Millennium Park, Cloud Gate (The Bean)
Soldier Field | Home to the NFL team the Chicago Bears
Magnificent Mile | Famous shopping district offering high-end fashion and more.
TimeOut Market | 50,000-sq.-ft offering the plethora of Chicago’s best food and cocktails.
The DuSable: Museum of African American History | Nation’s first independent museum dedicated to the collection, preservation and study of the history and culture of Africans and Americans of African descent.
Navy Pier | 3,300-foot-long pier on the shoreline of Lake Michigan
Gallery Guichard* | Gallery located in Bronzeville specializing in the art of the African Diaspora
Hotel Recommendations
Hotel EMC2
Where the intersection of art and science meet and the rooms are powered by Alexa to turn on the TV and order tolietries. Click here to see my room tour.
228 E Ontario St, Chicago, IL 60611
Soho House Chicago
Centrally located in Fulton Market District, where you can enjoy exclusive amenities like a professional boxing ring and the Cowshed spa.
113-125 North Green Street, Chicago, IL 60607
Swissôtel
Award-winning luxury hotel overlooking Lake Michigan and centered in wellness where they have an extensive fitness center that includes Peloton bikes and more. To see a complete room tour, click here.
323 E Wacker Dr, Chicago, IL 60601
additional food and beverage options
Food
Frontier | Rustic modern vibe, adventurous menu featuring wild game and whole animal options, and a lively atmosphere perfect for large groups
Gus’ Sip and Dip | Elevated tavern serves 30 mixed cocktails for $12 and offers a food menu that includes dipped sandwiches and more.
Trivoli Tavern | Chicago has a thing for taverns, but Trivoli’s is one of the best in the city, located in North Green Street’s historic courtyard.
La Grand Bourcherie | Swanky French restaurant located in the River North area.
Lula’s Cafe | James Beard award-winning farm-to-table restaurant in Logan Square offers breakfast, lunch, and dinner.
Bronzeville Winery* | Situated in the historic Bronzeville neighborhood, this restaurant focuses on Black- and woman-owned wines while offering a dinner menu, live music, and wine memberships.
Taylor’s Tacos* | Located in the Little Italy neighborhood, this woman-owned restaurant offers shrimp, chicken, sweet potato, and more tacos.
Maple & Ash | Steakhouse in Gold Coast is perfect for a celebration or a memorable dining experience for brunch or dinner.
Ann Sather’s | With multiple locations in the city, this is a must-stop for their warm and unforgettable cinnamon rolls, and grab a casual breakfast or lunch.
Cabra | Peruvian-inspired rooftop restaurant at the top of the Hoxton Hotel in Fulton Market District.
beverage
Ghost Donkey | Tequila bar is located in River North, offers a lively atmosphere, and works well with groups.
Drip Collective* | A coffee shop that provides a third space for many in Chicago to connect with like minds and attend events.
Nobody’s Darling | The James Beard-nominated LGBTQ cocktail bar in Andersonville offers a host of women and POC-owned spirits and wines.
Cantina Rosa* | Cocktail bar offering tapas honoring Mexican heritage in Hyde Park.
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