The most pivotal moments of Operation Midway Blitz, captured by Sun-Times photographers

When President Donald Trump launched “Operation Midway Blitz” in the Chicago area, he said it aimed to make the city safer.

Yet the increased presence of federal agents that started in September brought shootings, raids, protests, the deployment of less-lethal weapons, and fear to Chicago and its surrounding suburbs.

Here are some of the pivotal moments from the lenses of Chicago Sun-Times photojournalists.

Activists clash with federal immigration enforcement agents Sept. 12 outside the ICE facility in Broadview to protest the Trump administration’s deportation campaign.

Federal immigration enforcement agents detain a protester Sept. 19 outside the U.S. Immigration and Customs Enforcement facility in Broadview.

Federal immigration enforcement agents stand guard at the front gate outside the ICE facility in suburban Broadview on Sept. 22.

Armed federal immigration enforcement agents patrol the Chicago River on a U.S. Customs and Border Patrol boat Sept. 25 near North State Street and North Wabash Avenue.

Federal immigration enforcement agents detain a man during a skirmish with protesters Sept. 26 at South 25th Avenue and Harvard Street outside the ICE facility in Broadview.

Federal immigration enforcement agents stand guard outside the Broadview detention facility on Sept. 27.

A protester jeers at U.S. Immigration and Customs Enforecement agents behind the gate outside the Broadview detention facility on Sept. 27.

Federal immigration enforcement agents push protesters a block away from the Broadview ICE facility using tear gas and rubber projectiles on Sept. 27.

Steve Held, an independent journalist from Chicago, is arrested by federal immigration enforcement agents outside of the Broadview processing facility on Sept. 27.

Pedestrians share the crosswalk with federal U.S. Customs and Border Protection agents Sept. 28 on North Clark Street in River North.

Federal immigration agents and Illinois State Police troopers push protesters out of the roadway outside the U.S. Immigration and Customs Enforcement facility in Broadview on Oct. 3.

A federal immigration enforcement agent stands guard during a protest in the 3900 block of South Kedzie in Brighton Park on Oct. 4. — A federal immigration enforcement agent stands guard during an Oct. 4 protest in the 3900 block of South Kedzie in Brighton Park.

U.S Border Patrol agents deploy tear gas to push protesters out of the street Oct. 4 near West 39th St and South Kedzie Avenue in Brighton Park.

Federal immigration enforcement agents detain a protester in the 3900 block of South Kedzie Avenue in Brighton Park on Oct. 4. Protesters arrived at the scene after learning that a U.S. Border Patrol agent shot a woman in the area.

Illinois State Police troopers stand guard Oct. 3 near the U.S. Immigration and Customs Enforcement facility in Broadview.

A few dozen protesters rally in the approved protest zone on Beach Street outside the ICE facility in suburban Broadview on Oct. 10.

Fr. Dan Hartnett speaks with Illinois State Police Lt. Colonel Jason Bradley in an attempt to deliver Holy Communion to the people detained in the ICE processing facility in suburban Broadview on Oct. 11.

Emotional demonstrators kneel outside the U.S. Immigration and Customs Enforecement processing facility in suburban Broadview on Oct. 11.

A protester is arrested Oct. 11 by Illinois State Police at 25th Avenue and Harvard Street near the ICE processing facility in suburban Broadview.

Protesters gather Oct. 12 outside the U.S. Immigration and Customs Enforcement facility in Broadview as Illinois State Police keep guard.

A protester wearing an inflatable bee costume walks near the corner of 25th Avenue and Harvard Street after Cook County Sheriff’s police officers attempted to disperse protesters Oct. 12 near the U.S. Immigration and Customs Enforcement facility in Broadview.

A federal immigration enforcement agent points a crowd control weapon at a protester at East 105th Street and South Avenue N in the East Side on Oct. 14. Protesters gathered as U.S. Immigration and Customs Enforcement officers awaited the removal of their vehicle after it crashed during a pursuit.

U.S. Border Patrol Cmdr. Gregory Bovino stands with agents near the scene of a Oct. 22 car crash near Sam’s Club in Cicero. — U.S. Border Patrol Cmdr. Gregory Bovino stands with agents near the scene of an Oct. 22 car crash near Sam’s Club in Cicero.

U.S. Border Patrol Cmdr. Gregory Bovino holds a canister as he stands with agents during a skirmish with protesters Oct. 23 near West 27th Street and South Sacramento Avenue in Little Village.

Residents yell at federal immigration enforcement agents during a skirmish near West 27th Street and South Sacramento Avenue in Little Village on Oct. 23.

An individual is detained by federal immigration enforcement agents Oct. 24 at the 1100 block of North Wood Avenue in West Town.

Construction workers pause to watch and show support to protesters Oct. 25 as they march on West 26th Street in Little Village over recent federal law enforcement raids in the Chicago area, as part of Operation Midway Blitz.

A U.S. Border Patrol agent attempts to detain Christopher Klim, a U.S. citizen from Poland, in the 7400 block of North Oconto Avenue on the Northwest Side on Oct. 31. Klim was handcuffed but later released.

Protesters embrace during a standoff with Illinois State Police and Cook County Sheriff’s Police outside the U.S. Immigration and Customs Enforecement processing facility in suburban Broadview on Nov. 1.

Illinois State Police troopers clash with protesters outside the U.S. Immigration and Customs Enforecement processing facility in suburban Broadview on Nov. 1.

U.S. Border Patrol Cmdr. Gregory Bovino buys an energy drink and Slim Jims as he and a caravan of federal immigration enforcement agents stop at a Shell gas station Nov. 6 near West 53rd Street and South Kedzie Avenue on the Southwest Side.

Federal immigration enforcement agents stop a group of people to question their citizenship Nov. 6 as U.S. Border Patrol Cmdr. Gregory Bovino leads a caravan on the Southwest Side.

Residents yell, “He’s a U.S. citizen!” after federal immigration enforcement agents questioned a man about his citizenship Nov. 6 as U.S. Border Patrol Cmdr. Gregory Bovino leads a caravan on the Southwest Side.

A federal immigration enforcement agent looks out an SUV’s window as U.S. Border Patrol Cmdr. Gregory Bovino leads a caravan, making several stops to question residents on their immigration status, Nov. 6 on the Southwest Side.

U.S. Border Patrol Cmdr. Gregory Bovino stops near Fulton Avenue and Catalpa Street in Waukegan while leading a caravan of federal immigration enforcement agents Nov. 7, making several stops to question residents on their immigration status, in Waukegan and neighboring northern suburbs.

Protesters face off with Chicago Police Department officers at the intersection of 23rd St. and Sawyer Ave. in Little Village on Nov. 8.

Rafael Veraza holds his young daughter, Ariana, during a press conference Nov. 9 where they decried federal agents’ use of force in Little Village. Veraza and Ariana were pepper sprayed by federal agents while grocery shopping on Nov. 8.

Baltazar Enriquez helps kids get into a van to take them home outside of St. Agnes of Bohemia School in Little Village on November 14. It’s one of several community-led efforts that sprang up this fall to help children get to and from school safely as immigration enforcement activities intensified in Chicago.

Jason Perry sits in the kitchen of his trailer home in Boone, N.C. on Nov. 9. Perry wrestled with Gregory Bovino when they attended Watauga High School in the 1980s.

The border extending into the distance of United States and Mexico near Ocotillo, California. — The border extending into the distance of United States and Mexico near Ocotillo, California on Dec. 4.

Farm works pick produce in agricultural fields outside of El Centro, California on Dec. 6.

Homeland Security Chief Kristi Noem carries a Christmas tree during an annual Christmas tree charity event at Navy Pier on Dec. 6.

Protesters gather to speak out against United States Secretary of Homeland Security Kristi Noem’s visit at Navy Pier on Dec. 6.

Protesters attempt to toss back a chemical grenade outside an apartment complex in the 1600 block of Maple Lane, in suburban Elgin, Saturday, Dec. 6, 2025. | Tyler Pasciak LaRiviere/Sun-TimesELGINICE-120725-33.jpg — Protesters attempt to toss back a less-lethal munition outside an apartment complex in the 1600 block of Maple Lane in suburban Elgin on Saturday, December 6, 2025.

Federal immigration enforcement agents follow Border Patrol Cmdr. Gregory Bovino as they enter an icy alleyway Dec. 16 near West 27th Street and South Ridgeway Avenue in Little Village.

Federal immigration enforcement agents detain an individual Dec. 16 near West 27th Street and South Ridgeway Avenue in Little Village.

U.S. Border Patrol Cmdr. Gregory Bovino looks on after federal immigration enforcement agents detained an individual outside a Mobil gas station at 1950 Green Bay Rd. in Evanston on Dec. 17.

Federal immigration enforcement agents shatter a truck’s window and detain two men Dec. 17 outside a Home Depot at 2201 Oakton St. in Evanston.

Community members and rapid responders yell at federal immigration enforcement agents after they detained two men Dec. 17 outside a Home Depot at 2201 Oakton St. in Evanston.

Federal immigration enforcement agents perform a checkpoint and detain individuals in a rideshare lot near Balmoral Avenue and Mannheim Road in Rosemont near O’Hare International Airport on Dec. 17.

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The most pivotal moments of Operation Midway Blitz, captured by Sun-Times photographers

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