The 2019 mayoral election was a crowded race with 14 candidates vying for the top job.
Mayor Lori Lightfoot started off her 2020 budget preparations in late August with an invitation for elected officials to get serious about their pension crisis.
In October 2019, the CTU went on strike for 11 days, leaving Mayor Lori Lightfoot with a lot to juggle.
Mayor Lori Lightfoot fired police Superintendent Eddie Johnson in December 2019 after the discovery of Johnson asleep behind the wheel of his SUV became public.
At the start of 2020, along with new taxes going into effect, adults could legally buy and consume weed in Illinois.
In 2021, Chicago experienced the snowiest three weeks since 1979: Snowfall on Jan. 26 through Feb. 15 left 34.1 inches of snow at O’Hare International Airport.
In May 2021, Lori Lightfoot planned to fully reopen a lockdown-beleaguered city by the Fourth of July.
By May 2021, around the time of Mayor Lori Lightfoot’s two-year anniversary in office, at least a dozen top people in her administration had resigned.
In June 2021, the Tribune Editorial Board said Mayor Lori Lightfoot would have more wins on her policy agenda if she could better manage relationships.
In 2022, Mayor Lori Lightfoot had to choose between three bids for bringing a casino to Chicago.
Lori Lightfoot was afforded just 10 months of normalcy as mayor. Then came COVID-19.