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8 Fun Things To Do in Chicago This Weekend

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From Clockwise TLC, DJ Roy Davis Jr., Chicago Pride Parade, Glorilla, Future, G Herbo, Dwight White II and Shaggy (Photos: Facebook and Wikimedia Commons).

The first official weekend of Summer is here, and, as usual, there are many, many things you can get into. 

If you’re a music lover, then say less. This weekend is all about you. 

For the House Heads, there’s the Chicago House Music Festival at the Humboldt Park Boathouse. We can’t leave out the Hip-hop lovers. There’s the massive Lyrical Lemonade Summer Smash Festival at SeatGeek Stadium in Bridgeview.  

We also can’t leave out the Chicago Pride Parade, one of the largest gatherings of its kind in the world. It starts at noon on Montrose and Broadway in the Uptown neighborhood.

Whether you’re a low-key introvert or the life-of-the-party type, here are eight fun things to get into this weekend in Chicago. 

TLC, Shaggy, En Vogue & Sean Kingston (June 23)

You’ll be hard pressed to find a collection of hit making artists all on one bill like this one. TLC, Shaggy and En Vogue, in particular, were Billboard royalty in the 1990s and 2000s. And their bringing those hits to the Credit Union 1 Amphitheatre in Tinley Park. It should be a time.  

Chicago House Music Festival (June 23-24)

It’s house music all day and all night long in the city that birthed it. Here are the DJs that are expected to spin — DJ Roy Davis Jr., DJ Psycho-B, NoshaLuv, DJ Emmaculate, and DJ V. 

Pride in the Park Chicago 2023 (June 23-24)

This two-day festival returns to Grant Park with more music and revelry. Saweetie and DJ Lady D are the headliners for Saturday.

The Lyrical Lemonade Summer Smash 2023 (June 23-25) 

Some of the most popular and acclaimed Hip-hop acts in the galaxy will descend upon SeatGeek Stadium in Bridgeview for this three-day event. Future, Playboi Carti and Kid Cudi are the headliners. But the other acts are equally good: G Herbo, Freddie Gibbs, Glorilla, Vince Staples, Lil Uzi Vert, Cordae and even Ice Spice. Whew. 

Taste of Chicago Humboldt Park (June 24)

Expect great eats and beats as the Chicago House Music Festival hosts over 20 food vendors at the Humboldt Park Boathouse. House music performers will play on the main stage, and vendors will have an eclectic array of foods for sale.

Rhythm and Beats Chicago RnB+AfroBeats Block Party (June 24)

Dance your soul out at this glorious block party that features music from around the globe. This event takes place at City Hall (restaurant) by Fulton Market.

Something I Can Feel Art Gala (June 24)

This 3rd Annual Gala hosted by acclaimed Chicago artist Dwight White II promises a night of cultural immersion and creative excellence. This affair, which takes place at The Shops At Northbridge on the Mag Mile, will ultimately showcase Black excellence, from the art to the music and food.   

The Chicago Pride Parade (June 25)

The 52nd annual pride parade returns on the final Sunday of the month, and it might be the biggest one yet. Last year, the Pride Parade came back strong, attracting over one million revelers. Expect this year to be no different. 

About Post Author

Tacuma Roeback, Managing Editor

Tacuma R. Roeback is the Managing Editor for the Chicago Defender.

His journalism, non-fiction, and fiction have appeared in the Smithsonian Magazine, San Francisco Chronicle, Atlanta Journal-Constitution, The Tennessean, South Florida Sun-Sentinel, Phoenix New Times, HipHopDX.com, Okayplayer.com, The Shadow League, SAGE: The Encyclopedia of Identity, Downstate Story, Tidal Basin Review, and Reverie: Midwest African American Literature.

He is an alumnus of the Medill School of Journalism at Northwestern University, Chicago State University, and Florida A&M University.

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