
City Cast Chicago
๐ฉ๐ผโ๐ป Take the Milwaukee Avenue personality quiz
August 29, 2025 ยท โ Emmi Mack
Hey Chicago! On a recent walk, I found peace in River Park near Chicagoโs last waterfall. All I can say is get out there and take a stroll before the weather turns! Labor Day is fast approaching.

Now, onto the news and a special City Cast personality quiz ๐ฎ

What's CITY Talking About?
No Loan, No Guaranteed Pension Payment in CPS Budget
After nearly a year of conflict between the mayor's office and CPS leadership, the Chicago Board of Education approved a budget Thursday night. It does not include a loan for the debt-plagued district. It also relies on additional funds from the city that may or may not come. [WBEZ]

Why Are Some Students Without Classrooms?
As CPS waits to place about 200 students with disabilities in classrooms, Chalkbeatโs Samantha Smylie shares how families are managing. Also on todayโs podcast, Injustice Watch reporter Maya Dukmasova explains how a former UIC crime labโs questionable forensics science led to multiple cannabis DUI convictions. [City Cast Chicago ๐ง]
Beach Drummers Get the Boot in Woodlawn
Drummers and other musicians used to convene every day in a circle at 63rd Street Beach. This tradition, which began in 1970, ended abruptly in July, when the Park District fenced off the circle. The fence is part of a gated parking pilot, but the alderman hopes the drummers can get accommodations.ย [Block Club]

This Weekโs Must-Read
โWe were in hell, and now weโre in heaven,โ one Dolton bar owner put it. Between the scandals of recent Mayor Tiffany Henyard and the ascension of Robert Prevost to Pope Leo XIV, the struggling village is striving for reinvention. It just acquired the old Prevost house for $375,000 โย far less than its owner might have earned at auction. Meanwhile, the village faces a $3.65 million deficit. [Chicago magazine]
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Milwaukee Avenue Personality Quiz

Meet Me On Milwaukee! That's the idea of a new pilot program that will turn a stretch of Milwaukee Avenue in Wicker Park car-free on three separate days: Aug. 31, Sept. 28, and Oct. 26. The pedestrianization will reach from the intersection of North and Damen all the way to Ashland Avenue.
That corner of the city is always changing โ so is the diagonal street that cuts through it. Milwaukee Avenue is Chicago's bike highway. It has strong immigrant roots. It's also an artistic street, full of independent businesses stretching far beyond the confines of Wicker Park.
How you spend a day on Milwaukee says a lot about you. Take this quiz to determine your Milwaukee Avenue Personality (and learn which City Cast Chicago team member shares your type)!
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What To Do
Friday, Aug. 29
- ๐ Luya Poetry 7th Anniversary Celebration | California Clipper | Humboldt Park
- ๐ต๐ฑ Taste of Polonia | Copernicus Center | Jefferson Park
- ๐ฃ Youth Civics Dialogue | Chicago History Museum | Lincoln Park
- ๐ถ๐ปโโ๏ธWalking Tour: Paseo Boricua and Humboldt Park | Ciclo Urbano
- ๐ค My Chemical Romance + Devo | Soldier Field
- ๐ถ๐ฝโโ๏ธ Walking Tour: Glitterati on the Gold Coast | Chicago History Museum | Lincoln Park
- ๐ธ Rockin' in the Park | Parkway Bank Park | Rosemont
- ๐ต Skyline Sessions | Navy Pier
- ๐ North Coast Music Festival | Seatgeek Stadium | Bridgeview
- ๐ถ ARC Music Festival | Union Park | Near West Side
- ๐ท Chicago Jazz Festival | Chicago Cultural Center and Millennium Park | Loop
- ๐ธ๐ช Anders Knutsson: Artist Talk | Swedish American Museum | Andersonville
- ๐ช Bodybuilder | Point Blank | Logan Square
Saturday, Aug. 30
- ๐ถ๐ปโโ๏ธ Walking Tour: Pilsen Murals | National Museum of Mexican Art
- ๐ต๐ฑ Taste of Polonia | Copernicus Center | Jefferson Park
- ๐ WingOut Chicago | Gallagher Way | Wrigleyville
- ๐คผโโ๏ธ Lucha Libre | Unity Park | Logan Square
- ๐ Wave Wall Wax | Navy Pier
- ๐ฏ๏ธ Candlelight: Neo-Soul Favorites | Wicker Park Lutheran Church
- ๐ African Festival of the Arts | DuSable Museum | Washington Park
- ๐ North Coast Music Festival | Seatgeek Stadium | Bridgeview
- ๐ถ ARC Music Festival | Union Park | Near West Side
- ๐ท Chicago Jazz Festival | Chicago Cultural Center and Millennium Park | Loop
- ๐ช Summer Workouts | Millennium Park | Loop
- ๐ผ๏ธ Far From Somewhere | The Block House Gallery | Pullman
- ๐ฅ Funeral at the Movies | Bodenrader | West Loop
- ๐ Summer Fireworks | Navy Pier
- ๐ All for Print. Print for All. | Harold Washington Library | Loop
- ๐๏ธ Elizabeth Catlett: A Black Revolutionary Artist and All That It Implies | The Art Institute of Chicago | Loop
- ๐ฅ Yukimasa Ida: Flaming Memory | Mariane Ibrahim Gallery | West Loop
- ๐ผ๏ธ 8th Midwest Open | Woman Made Gallery | Little Italy
Sunday, Aug. 31
- ๐ด๐ปโโ๏ธ Bike the Drive | Grant Park
- ๐ณ Humboldt Park Arboreal Society (DJs) | Noon to Sundown | Free | Humboldt Park
- ๐ North Coast Music Festival | Seatgeek Stadium | Bridgeview
- ๐ต๐ฑ Taste of Polonia | Copernicus Center | Jefferson Park
- ๐ WingOut Chicago | Gallagher Way | Wrigleyville
- ๐ป Kolsch Service | Salt Shed Pub | Goose Island
- ๐ถ๐ป Walking Tour: Historic Prairie Avenue | Glessner House | Near South Side
- ๐ African Festival of the Arts | DuSable Museum | Washington Park
- ๐ฅ Another Vegan Market | Emporium | Logan Square
- ๐ท Lil Piggy Market | The Native | Logan Square
- ๐ถ ARC Music Festival | Union Park | Near West Side
- ๐ท Chicago Jazz Festival | Chicago Cultural Center and Millennium Park | Loop
- ๐ฏ๏ธ Natural Incense Workshop | Empty Bottle | Ukrainian Village
- ๐ผ๏ธ Day of Leisure | Leisure | Ukrainian Village
- ๐ 10 Year Anniversary Celebration | 345 Art Gallery | East Garfield Park
Monday, Sep. 1
- ๐ช Workers over Billionaires | Haymarket Memorial | West Loop
- ๐ท 8th Annual Labor Day Jazz Festival | Jazz Showcase | South Loop
- โพ๏ธ Cubs vs. Braves | Wrigley Field
- ๐ต๐ฑ Taste of Polonia | Copernicus Center | Jefferson Park
- ๐ African Festival of the Arts | DuSable Museum | Washington Park
- ๐ธ Live on the Lake! | Navy Pier
- ๐บ๐ป Free Mondays | Empty Bottle | Ukrainian Village
- ๐ค Punk Rock Mondays | Delilahโs | Lincoln Park
- ๐ Farmers Market | 5917 N. Broadway Ave. | Edgewater
- โ๏ธ Adult Creative Writing Group | Portage-Cragin Branch | Belmont Cragin
- ๐ค Viva La Raza Tour | Plaza Garibaldi | South Lawndale
- ๐ข Labor Day Cruise on Lake Michigan | Monroe Harbor | Loop
๐ I hope you have a restful โ who am I kidding, I hope you have a lit โ holiday weekend! Hey Chicago will be back in your inbox Tuesday morning.
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