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Cubs and White Sox Reached the Playoffs. Here’s What to Expect in the Wild Card Series

This marks the first time since 2020 that both Chicago teams made the postseason. Both teams will play their best-of-three Wild Card Series on the road starting Tuesday with the Cubs taking on the Padres in San Diego and the White Sox facing the Astros in Houston.

Week in Review: Parking Meter Sale Advances; Cubs and Sox Clinch Playoff Spots

Chicago’s much-hated parking meter deal could get a little bit better. And should serious police discipline cases be heard behind closed doors?

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Future Remains Uncertain for Two Chicago-Area Safety-Net Hospitals Under New Ownership

Insight Health Systems reached a deal last week to purchase both Weiss Memorial Hospital in Uptown and West Suburban Medical Center in Oak Park after both shuttered following years of reported mismanagement and poor structural conditions.

‘Deal of the Century’: Sale of Chicago Parking Meters to Investment Firm Advances

“We have an opportunity to not only apologize to Chicagoans for the city’s past mistakes, but to back that apology with real, tangible benefits for taxpayers for the first time,” Ald. Pat Dowell (3rd Ward) said.

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Sept. 24, 2026 - Full Show

What’s in the revamped parking meter deal. And two closed safety-net hospitals get new ownership.

Sept. 23, 2026 - Full Show

City Council approves plans for more affordable housing. And could a 32-hour workweek become the new standard? We unpack the proposal.

Chicago Mayoral Candidate Willie Wilson on Hiring Police, Cutting Taxes and Balancing the Budget

Chicago businessman and philanthropist Willie Wilson is throwing his hat in the ring for mayor of Chicago — his fourth bid for City Hall’s fifth floor. Wilson also ran for U.S. president in 2016 and for the U.S. Senate in 2020.

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New Bill Would Create a 32-Hour Workweek in the US. Here’s What to Know

U.S. Sen. Bernie Sanders (I-Vermont) and U.S. Rep. Mark Takano (D-California) reintroduced the Thirty-Two Hour Workweek Act. The bill has undergone several revisions since it was first introduced in 2021 and now faces lawmakers for the fourth time.

City Council Approves Plans for 200 Affordable Homes in Edgewater, Humboldt Park

The two long-in-the-works developments will get city subsidies totaling $57.6 million, including the first large chunk of funds from Mayor Brandon Johnson’s signature economic development effort.

Sept. 22, 2026 - Full Show

A legal challenge over the Chicago Police Department’s disciplinary process. And competing renters’ rights ordinances make their way to City Council.

Fate of Chicago Police Reform Push at Stake Ahead of Illinois Supreme Court Arguments: Attorney General

The Illinois Supreme Court will hold oral arguments Thursday amid a legal dispute between the city of Chicago and the city’s largest police union that has lasted for more than two years.

City Officials Want to Step Up Protections for Renters. Here’s What to Know About the Competing Proposals

Here’s a breakdown of what the two proposals to rewrite Chicago’s 40-year-old landlord-tenant law would do and what’s at stake.

3rd Rescued Beluga Dies at Shedd Aquarium. Remaining Whales’ Outcomes Are ‘Day by Day, Hour by Hour’

Shedd Aquarium shared the disheartening news of another death among the beluga whales it rescued this summer from a defunct marine park in Canada.

Sept. 21, 2026 - Full Show

What’s behind the skyrocketing cost of diesel? And the head of the Smithsonian on his decision to step down amid battles with the Trump administration.

As the Iran War Continues, Diesel Prices Hit All-Time High

Diesel surpassed $6 per gallon for the first time in U.S. history earlier this month, according to data from AAA. Today, diesel sits at $6.51 per gallon, an all-time high. A year ago, it was $3.69. The cost of diesel rose 42 cents last week alone.