Also, Chicago’s oldest bar  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
Monday, June 22 

Your Daily Guide

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.

The bottom half of a woman and a man on a stage with a mic. The woman has an old photo of a woman printed on her dress

“Marion would have been so proud, was so proud, of her son-in-law,” said Former First Lady Michelle Obama. (Pablo Martinez Monsivais / POOL / AFP via Getty Images)

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!

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What Chicago's Talking About

PODCAST

City Will Buy Greyhound Terminal, Chicago's 'Friendship Recession,' and We Want 4 a.m. Tacos!

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]

A neon sign that says "Bowl Restaurant"

A favorite sign of mine: Diversey Bowl. (Emmi Mack / City Cast Chicago)

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]

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What is your library story?

Hello, fellow library lovers. We are collecting love letters for our Chicago Public Library, and we’d like to hear from you. Submit your story and get a gift from the Chicago Public Library Foundation!

Test Your Knowledge of the Obamas in Chicago

From left to right Malia, Sasha, Michelle, and Barack Obama sitting and smiling at each other behind a glass pane. Behind them from left to right sits George W Bush, Laura Bush, and Bill Clinton

The former first family at Thursday’s Obama Presidential Center opening event. (Kent Nishimura / AFP via Getty Images)

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.

We’ll start with a super easy one: What high school did Michelle go to?

Lane Tech

Whitney Young

Kenwood Academy

Walter Payton

🤓 Can you get 5/5?
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What To Do

Monday, June 22

Tuesday, June 23

More Chicago Events
A vibrant circus stage with performers in colorful costumes. Aerialists swing gracefully above, while a ringmaster commands attention below, creating a lively scene.

The bestselling novel is now a spectacular new musical!

WATER FOR ELEPHANTS comes to life on stage featuring puppetry, acrobatics and circus stuntwork that The New York Times calls “stunning, emotional, heart-filled and gorgeously imaginative.” After a young man jumps a moving train, he finds a new home with a traveling circus, and a life—and love—beyond his wildest dreams. Playing at the James M. Nederlander Theatre from June 23 to July 5 only. Step right up and get your tickets!

🍻 Have you been to Chicago’s (confirmed) oldest bar?

— Emmi Mack

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