They blame poor police morale on the man Mayor Daley brought in to change things in 2008.
The Fraternal Order of Police (FOP) promised thousands would march on headquarters to show their disdain for their boss. While the numbers weren't that big, the group was noisy and upset.
The FOP requested that Jody Weis resign from his position as superintendent.
With vocal demands and chants, about 300 police officers - most active, many retired, many with family in tow - crowded police headquarters on S. Michigan Avenue.
After two years on the job and facing a contract renewal next march, they are pinning Jody Weis with a range of shortcomings that the protestors say make him unfit to be Chicago's top cop.
"We've had seven police officers shot so far this year - three of them fatally - how many more will it take until we get the resources to do our job?" said FOP President Mark Donahue.
A summer that saw multiple police funerals has led police union members to grumble publicly about Weis's performance.
Complaining union members are upset that the department's staffing remains about 2,000 officers below mandated levels. They bristle at Weis's decisions, especially deploying more officers to three tactical squads, and decimating, in their words, the effectiveness of the beat cop
"You build trust in the community when they know who the beat cop is that works their neighborhood and they can trust that person," said the 11th District Watch Commander, Lt. John Andrews. "Well, we have so few police officers working at district patrol now that they are just running from call to call - there is no time for any proactive policing."
"You gotta be realistic. Some people are going to complain. You can give them a gold brick and they're going to complain how heavy it is," said Weis on Tuesday. "What we have to do is focus on people that want to do a good job and get the tools they need to do a good job."
A feisty Weis on Tuesday rejected calls for his resignation, saying he was brought in to fix a department many saw as adrift and reeling from bad press over the indiscretions of off-duty officers.
His work appears cut out for him in regaining the trust of those he leads.
"You know you get that lump in your throat any time you hear of a shooting, every time a police-related shooting your nerves are just wrecked because you know you are out there alone every night," said career Chicago police officer Judy Fudacc.
The union says it recognizes budget constraints, but says there is no price tag to be put on safety.
The debate over deployment is the latest dispute in a relationship with the union that long ago soured for Weis, a career FBI agent who has often been criticized as an outsider who is out of sync with Chicago street officers.