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Afternoon Briefing

Monday, October 20, 2025

Good afternoon, Chicago.

A federal judge in Chicago is grilling a pair of immigration officials today about law enforcement tactics employed during the Trump administration’s ongoing “Operation Midway Blitz” that allegedly are in violation of a restraining order she issued earlier this month.

U.S. District Judge Sarah Ellis said last week she was “profoundly concerned” that immigration agents are violating her orders restricting the use of tear gas on media and protesters, and told the Department of Justice to make officials with knowledge of the operation to appear before her and answer questions.

Here’s what else is happening today. And remember, for the latest breaking news in Chicago, visit chicagotribune.com/latest-headlines and sign up to get our alerts on all your devices.

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news
Mayor Brandon Johnson speaks during the “No Kings” rally and march on Oct. 18, 2025, in Chicago. (John J. Kim/Chicago Tribune)

Chicago Mayor Brandon Johnson sues Trump over threat to cut emergency funding

The city’s federal suit, filed today, alleges the Department of Homeland Security has tied long-standing funding that pays for cybersecurity tools, hazmat suits, first responder salaries and more to “unlawful conditions” outlawing the city’s “diversity, equity and inclusion” efforts.

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business
The Amazon Web Services booth at the National Retail Federation’s annual trade show is seen in January 2020 in New York. (Maria Halkias/Dallas Morning News)

Amazon cloud computing outage disrupts McDonald’s app, Snapchat and many other online services

A problem at Amazon’s cloud computing service disrupted internet use around the world early today, taking down dozens of online services, including social media site Snapchat, the Roblox and Fortnite video games and chat app Signal.

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sports
The Blackhawks’ Ryan Donato scores the winning goal against Ducks goalie Lukas Dostal and Mason McTavish (23) in overtime, Oct. 19, 2025, at the United Center. (AP Photo/Paul Beaty)

Chicago Blackhawks beat former coach Joel Quenneville’s Anaheim Ducks as Ryan Donato scores in OT

The Hawks defeated the Ducks 2-1 in overtime as Connor Bedard ended his high-quality night with a pass to Ryan Donato, who sounded the horn for the team’s third win of the season.

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eat. watch. do.
Artistic Director Carling FitzSimmons, left, and Alana Grossman, sing during La Caccina’s rehearsal for their fall concert, “Weird Sisters,” on Oct. 6, 2025. FitzSimmons is one of the original members of the group when it was founded in 2011. (Anastasia Busby/for the Chicago Tribune)

Meet La Caccina, the choir celebrating strong women — and, this Halloween, witches

To try to summarize what La Caccina does is a tall order. The treble choir’s witch-themed “Weird Sisters” — Oct. 25 and 26, just in time for Halloween — stretches from “W.I.T.C.H.,” Devon Cole’s viral pop hit from 2022, to Swedish composer Arne Mellnäs’ 1969 piece “Aglepta.”

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nation & world
People gather to welcome freed Israeli hostage, Elkana Bohbot, who was recently released from Hamas captivity in Gaza, as he returns home from the hospital to Mevaseret Zion, Israel, Oct. 19, 2025. (AP Photo/Francisco Seco)

US envoys arrive in Israel to shore up the Gaza ceasefire after a major flareup

Special envoy Steve Witkoff and the U.S. president’s son-in-law Jared Kushner were in Israel today to shore up the tenuous ceasefire that’s holding in Gaza, a day after the fragile deal faced its first major flareup.

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