Racial tensions have soared in the US city over the shooting of 17-year-old Laquan McDonald, for which a white police officer was charged this week with first-degree murder.
Graphic footage of the October 2014 shooting has set Chicago on edge and reignited angry debate about the use of force by US law enforcement.
Protesters thronged Chicago's "Magnificent Mile" where police and private security guarded upmarket outlets like Tiffany and Co. And the Apple Store, locking arms in front of stores to keep shoppers from entering.
A group of Black Power activists marched with red, green and black flags chanting "You can't see it and hide no more" while civil rights leader Jesse Jackson led a separate group in a more solemn march.
Also Read
Tensions flared in the highly-segregated Midwestern city after officials released a dashcam video this week showing officer Jason van Dyke fire 16 bullets at the teenager.
Prosecutors and city officials have been accused of trying to block the footage's release and criticized for waiting until this week to press charges.
Protesters say the shooting illustrates deeper injustices both in Chicago and nationwide.
Many liken McDonald's case to that of Michael Brown, the black teenager shot dead by a white policeman in Ferguson, Missouri last year, whose death triggered 15 months of demonstrations over perceived police brutality against black men.