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.  

You can sign up for their free 2022 guide by clicking here, which is how I created my itinerary for this trip and my own research.

* 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.

Dinner @ The Signature Room at 95th
Known for its iconic views of the Windy City and serves American fare and reservations are required.
875 N Michigan Ave, Chicago, IL 60611

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.

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.

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

Exhibit @ Immersive Frida Khalo
A 35-minute loop that which the art and life of Frida Khalo play out on the walls.
108 W Germania Pl, Chicago, IL 60610

Dom’s Tip: Be sure to wear comfortable clothing as seating is limited and may require you to sit on the floor.

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.

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

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

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