Chicago’s 2025 Highlights: Tragedies, Triumphs, and Change

URGENT UPDATE: As 2025 draws to a close, Chicago has witnessed a year filled with pivotal events that will shape its future. From the historic election of a Chicago-born pope to devastating local tragedies, the city’s resilience has been put to the test.

Key moments include: the passing of Chicago Bears matriarch Virginia McCaskey, the sobering impact of Operation Midway Blitz, and the tragic death of Officer Krystal Rivera. These events not only resonate with residents but also reflect broader societal issues that demand urgent attention.

In January, Chicagoans kicked off the year with a vibrant Countdown Chicago event, featuring a memorable dance performance that filled the city with hope. However, the optimism soon faced challenges as Ben Johnson was appointed as head coach of the Chicago Bears, igniting excitement among fans eager for a turnaround.

February marked a period of mourning as Virginia McCaskey, a cornerstone of the Bears’ legacy, passed away at 102 years old. Her contributions to the team and the community will be remembered for generations. The month also saw former Illinois governor Rod Blagojevich receive a full pardon from President Donald Trump, wiping his record clean, while another political figure, Michael Madigan, faced a starkly different fate, being convicted of corruption.

March brought closure to a painful chapter for Highland Park as Robert Crimo III pleaded guilty to charges related to the mass shooting during the 4th of July parade, a tragedy that left seven dead and many more injured. Meanwhile, a decades-old missing persons case was resolved when the remains of Karen Schepers were discovered in the Fox River, providing answers to a grieving family.

In April, a shocking attack at DePaul University saw two Jewish students brutally assaulted, leading to charges of hate crimes that sparked widespread outrage. The month also marked the passing of Chicago Bears legend Steve “Mongo” McMichael, who died after a courageous battle with ALS.

The election of Pope Leo XIV in May, born Robert Francis Prevost in Chicago, elevated the city’s profile on the global stage, inspiring many, including local students. However, the month also saw an unprecedented dust storm warning issued for the area—a rare weather phenomenon that captivated residents.

As the summer unfolded, tensions flared over education funding when Chicago Public Schools CEO Pedro Martinez resigned amidst fierce debates over high-interest loans for teacher contracts. In June, fears of an immigration crackdown intensified as local leaders confronted federal agents during protests, marking a significant moment in the ongoing national conversation about immigration policy.

Tragedy struck in July with the accidental shooting death of Officer Krystal Rivera, leaving the Chicago Police Department and the community in mourning. That same month, River North was rocked by a mass shooting at a local rapper’s album release party, injuring 18 people and claiming four lives in a shocking act of violence.

August saw the Chicago Bears hinting at a potential move from Soldier Field to Arlington Heights, while the Chicago Air & Water Show captivated audiences despite reports of shattered windows along the lakefront.

In September, the federal government’s Operation Midway Blitz commenced, resulting in hundreds of arrests related to illegal immigration, facing fierce protests from local communities. The assassination of political activist Charlie Kirk on a college campus in Utah added to the growing list of violent incidents troubling the nation.

October brought more sorrow with the passing of beloved Loyola University basketball figure Sister Jean at 106 years old, and a helicopter crash tragically claimed the lives of Darren Bailey‘s family members, prompting the candidate to remain steadfast in his gubernatorial race.

November dazzled Chicagoans with a rare appearance of the northern lights, providing a moment of beauty amid the chaos. However, a shocking crime on a CTA train, where a woman was set on fire, ignited calls for improved safety measures across the transit system.

As December approached, the city announced a significant reconstruction project for the State and Lake ‘L’ station, set to close for three years. Mayor Brandon Johnson faced challenges in finalizing the city budget, navigating conflicts over a proposed corporate head tax to address fiscal deficits.

As Chicagoans reflect on 2025, the year undeniably stands as a testament to resilience, community spirit, and the ongoing fight for justice and safety. The developments of this year will resonate well into the future, urging residents to stay vigilant and engaged in shaping their city.