City Cast Chicago
🧠 The Obama-Chicago trivia quiz
June 22, 2026 · — Emmi Mack
Wow, Chicago. Let’s take another moment to acknowledge a Michelle Obama fashion moment equal parts iconic and meaningful: a custom Acne skirt featuring her late mother, Marion Robinson.
I know, I know, it was a long weekend of Obama news. Now let’s see if you were paying attention. Today’s newsletter features a quiz on the Obamas in Chicago — yes we CAN keep this going just a little longer!
What's CITY Talking About
Greyhound Terminal Purchase
On today’s podcast, we discuss what’s next for the Greyhound bus terminal, as the city now plans to buy the station. Also: Is Chicago in a friendship recession, and what spots SHOULD be open till 5 a.m.? [City Cast Chicago 🎧]
A Long Wait For Sewer Repairs
West Siders are still waiting for basement repairs after the historic 2023 storms. But flooding and damage will only get worse if the city doesn’t fix the area’s aging pipes — more than 250 miles of “deficient sewers” in all. [Sun-Times]
Police Misconduct Settlements FAR Outpace Budget
Police misconduct settlements reached $225 million in the first half of 2026. The city budgeted just $82.5 million for settlements for the whole year, with authorization to borrow an additional $283.3 million. [WTTW]
Hate Crime Charges Filed Against Man Who Lit Burning Cross
Hate crime charges were filed against 21-year-old Merlin Lu. Lu admitted to burning a cross in Grant Park, claiming the act was in protest of President Donald Trump. [NBC 5]
Who Still Makes Neon in Chicago? This Guy!
Neon Shop Fishtail in Logan Square has been in business for 40 years. Owner Tom Brickler and his team make neon for Chicago businesses, as well as movies and TV shows. Brickler likes to think of himself as the “Godfather of Neon”: “I’ll make you a neon offer you can’t refuse.” [Block Club]
- Meanwhile: Chicago is losing neon signs 😢 [City Cast Chicago 🤳]
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Test Your Knowledge of the Obamas in Chicago
Juneteenth weekend was extra bustling in Chicago this year, thanks to the Obama Presidential Center opening. The big party was Thursday night, followed by three more days of activities and performances.
It’s no surprise the city went so hard for Barack Obama — love him or hate him, he’s a Chicago legend. The same goes double for Michelle.
See how well you know their Chicago roots.
What To Do
Monday, June 22
- 🌿 Free admission | Peggy Notebaert Nature Museum | Lincoln Park
- ⚾ Toy Story Night at Sox vs. Guardians | Sox Park | Bridgeport
- 📽️ “Sarah’s Oil” | Taylor Park | Grand Boulevard | Free
- 🎶 Summer Music Series | Millennium Park | Loop | Free
- ⚡️ Laser tag | Gill Park | Lakeview | Free
- 💋 Tassels and Tunes Burlesque | The Owl | Logan Square | Free
- 🪘 Afrobeats on the beach | Pier 31 | Bronzeville | Free
- 🎣 Go Fishing with Jonathan | Marquette Park | Free
Tuesday, June 23
- 🖼️ Tuesdays at the Terrace | Museum of Contemporary Art Chicago | Streeterville | Free
- ⚾ Sox vs. Guardians ($5 Tuesday) | Sox Park | Bridgeport
- 🐟 Free night | Shedd Aquarium | Museum Campus
- 🎷 Jazz’n in the Parks | Meyering | Greater Grand Crossing | Free
- 🦋 Free Day | Peggy Notebart Nature Museum | Lincoln Park
- 📖 Media Burn Picnic | Media Burn Archive | Near West Side | Free
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🍻 Have you been to Chicago’s (confirmed) oldest bar?
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