As of this month, Chicago is out another $22 million in police misconduct payouts. First, the city settled one lawsuit—brought by the family of Bettie Jones, an innocent bystander shot by police officer Robert Rialmo, who also killed Quintonio LeGrier in December 2015—for $16 million. A few days later, the City Council authorized a $6 million payment for two other police misconduct settlements.  A report about the cost of police misconduct settlements and judgments recently published by the Action Center on Race & the Economy, a group that researches racial injustice in the financial industry, estimates that Chicago has paid out more than $800 million for police misconduct lawsuits since 2004. The price tag could climb to more than $1 billion dollars when the cost of using bonds (aka borrowed money) to make these payments is factored in. 
Here’s why this discussion is currently moot in Chicago: Since 1945, the state of Illinois has required the city to indemnify police officers. This means that the city, not the officer, has to pay out settlements and judgments when cops are sued in their official capacity. Though the law says that cops are not supposed to be indemnified “where the injury results from the willful misconduct of the police officer,” in practice, no matter how egregious the situation, the city has always covered misconduct settlements and judgments.