
City Cast Chicago
🛍️ Street markets, Sueños, and cookouts!
May 22, 2026 · — Michelle Navarro
Hey Chicago! So much is going on this weekend:
- 💃 Tonight, catch a free cumbia lesson in Humboldt Park.
- 🎶 Sueños, the largest all-Latino music festival in the Midwest, returns to Grant Park Saturday and Sunday for the 5th year in a row.
- 🛍️ The Randolph Street Market in West Loop for arts, antiques, and vintage is also back Saturday and Sunday, rain or shine.
- 🍽️ Then, on Monday, top it off with a classic Memorial Day cookout in Uptown.
Now, let’s get into the news and your weekly news quiz!

What's CITY Talking About

City Council’s Tipped Wage Compromise
City Council met earlier this week with a lengthy to-do list. On today’s podcast, we discuss the near-unanimous vote delaying the tipped minimum wage hike. Here are other measures alders approved:
- An affordable housing portal with information on units, providers, and waitlists. [Block Club]
- The $54.7 million property tax break for the 1901 Project, which will turn parking lots surrounding the United Center into residential and entertainment developments. [Sun-Times]
- An ordinance to rid the police department of officers with ties to extremist groups, like Proud Boys and Oath Keepers. [WTTW]
CHA Board Chair May Run For Mayor
Local business leaders say Matthew Brewer has been making the rounds to float a 2027 run. He’s been openly beefing with Mayor Brandon Johnson over leadership at the Chicago Housing Authority. Johnson has not yet committed to running for a second term, but the race could be crowded. [Sun-Times]
- What’s the beef? Johnson tried to oust Brewer following the appointment of a new head of CHA. [City Cast Chicago 🎧]
Zillow Gets Cut Off
Midwest Real Estate Data, Chicago’s main home listing service, yanked Zillow’s access shortly after Zillow filed an antitrust suit against MRED and the massive brokerage Compass. MRED and Compass recently joined forces to launch a nationwide private-listing network. Zillow says the move will mean “hiding homes” and “cutting off competition.” [Chicago Agent]
- As a result, thousands of Chicago listings vanished from Zillow. [Sun-Times]
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The Middle of Everything
Ever notice how the best part of anything is right in the middle? Come see for yourself in Illinois, where you can hit the trails in breathtaking state parks. Experience classic Americana on Route 66. And even kayak through a glistening canyon of skyscrapers. It’s all right here in Illinois.

Your Chicago News Quiz

How well do you keep up with the news? Test your knowledge by taking our weekly Chicago news quiz!

Neighborhood Shoutouts
When you become a City Cast Chicago Neighbor, you get the chance to shout out your favorite local gems.
Our neighbor Brandon W. is shouting out Queen B in Lakeview. He says it's one of the best cinnamon rolls in the city!
Sponsored Content

Chicago’s Free Literary Weekend featuring Award-Winning Writers
Bestselling storytellers come together for the American Writers Festival, June 6–7. Presented by the American Writers Museum in partnership with the Chicago Public Library, the festival features in-depth with writers across genres, plus workshops, storytimes, book signings, and family-friendly activities for attendees of all ages.
Events run from 10 a.m. to 5 p.m. both days, with programming at the American Writers Museum on June 6 and Harold Washington Library Center on June 7. Learn more at AmericanWritersFestival.org.

What To Do
Friday, May 22
- 🎭 Broadway Rave | Subterranean | Wicker Park
- 🎵 Belmont-Sheffield Music Fest | 3200 N. Sheffield | Lakeview
- 🖼️ Studio Sale | Arts of Life | West Town
- 🎨 “Too Much, Not Enough II” opens | Logan Center | Woodlawn
- 💃 Cumbia Lesson | Humboldt Park | Free
- 🖤 World Goth Day | Gman Tavern | Wrigleyville
- 🎧 Sueños Pre-Parties | Various Locations
- 💿 Electric Feel | Beauty Bar | West Town | Free
- 🖼️ Open Studios | Bridgeport Art Center | Free
Saturday, May 23
- ☀️ Englewood Safe Summer Kickoff | Hamilton Park | Free
- 🎶 Sueños | Grant Park | Loop
- 💐 Memorial Day Wreath Laying and Parade | Daley Plaza | Loop | Free
- 🛍️ Randolph Street Market | 1341 W. Randolph | West Loop
- 🖼️ Mañanas en el Museo | National Museum of Mexican Art | Pilsen | Free
- 🎤 Warm Love Cool Dreams | Salt Shed | West Town
- 🎵 Belmont-Sheffield Music Fest | 3200 N. Sheffield | Lakeview
- 🐦 Early Bird Walks | North Park Village Nature Center | Free
- 🎧 Perreo Obscuro | Simone’s | Pilsen | Free
- 🦠 Germ Party | International Museum of Surgical Science | Gold Coast
- 🧘 Cacao & Sound Bath Meditation | Walker Branch | Morgan Park | Free
Sunday, May 24
- 🎨 Black Boy Art Show | Navy Pier
- 🎶 Sueños | Grant Park | Loop
- 🛍️ Randolph Street Market | 1341 W. Randolph | West Loop
- 🎤 Warm Love Cool Dreams | Salt Shed | West Town
- 🚶 Walking History | Douglass Park | Free
- 🎵 Belmont-Sheffield Music Fest | 3200 N. Sheffield | Lakeview
- 🎃 Halfway to Halloween Market | 1657 N. Kostner | Humboldt Park
- 🗑️ Community Cleanup | Elm Park | Hyde Park | Free
- 🧺 Singles Picnic | Wicker Park Farmers Market
- ⚾ Bobblehead Night | Wrigley Field
You can now vote to name the South Side's baby bald eagle until June 1. I voted for Migizi, the Ojibwe word for "Bald Eagle." It has a nice ring to it.
Free · Daily



