Mar 8, 2024 - Culture

Rashida "Sheedz" Olayiwola's Best Day Ever in Chicago

Photo of a woman posing with a jacket on

Photo courtesy of Kevin Scanlon

Rashida "Sheedz" Olayiwola is having a great year, and it's only March.

State of play: The Chicago-born comedian and writer is cashing in on her hilarious turn as a bailiff in the Emmy-nominated Amazon TV show "Jury Duty."

  • The former "South Side" writer was also chosen to participate in the 2024 CBS Showcase, highlighting up-and-coming talent in the entertainment industry.

Zoom in: With all the appearances on red carpets in Hollywood and New York, Olayiwola remains unapologetically Chicago. She spent years here doing comedy but also working with youth on the South Side.

So Axios asked her to give us her perfect day in her hometown.

Photo of the front of a restaurant
Valois on 53rd Street in Hyde Park. Photo: Justin Kaufmann/Axios

🍳 Breakfast: Valois in Hyde Park. "I order the ham, egg and cheese on toast with a fruit punch Kool-Aid. And if I feel like balling that day, I'll get the Obama Special (steak and eggs) with some grits."

👟 Morning activity: "Walk on the lakefront from 67th Street Beach to about 47th Street Beach, where you can see the skyline and sit, chill and talk with somebody."

😋 Lunch: Portillo's! "I get Italian beef, double dipped, sweet and hot peppers, and absolutely NO CHEESE."

Photo of the outside of a record store
Hyde Park Records. Photo: Justin Kaufmann/Axios

🎵 Afternoon activity: "I'd shop on Rush Street or hit up Hyde Park Records. I love music and all the cool stuff there. Then I'd go across the street to the Silver Room and grab some merch."

  • "After that I would go to Sip and Savor for a Chai Tea. And if it's spring time, I'd hit up a Sox game. Soxside baby!"

🍗 Dinner: Provaré in West Town or Phlavz off Maxwell Street. "Both have amazing food, are Black owned, operated by two of my college buddies, and doing extremely well."

Photo of a skyline
The view of Chicago's skyline from the Adler Planetarium. Photo: Justin Kaufmann/Axios

🌟 Evening activity: "Take a sunset cruise, look at the stars at the Planetarium, throw a penny in the Buckingham Fountain, and hit up Kingston Mines for some jazz and blues. I love being a tourist in my own city, so dope."

🚙 After-party spot: "I really love Tribe Chicago. They always have good music and good vibes. Then a 15-mile drive down Lake Shore Drive with a great playlist. That's the best."

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