Off-duty cop, 3 bicyclists, and a concealed carry holder are among the victims targeted in Chicago’s latest robbery sprees

The approximate locations of the robberies included in this report. | Multiplottr

CHICAGO — It wouldn’t be a new day in Chicago if we weren’t here to tell you about all of the robberies that have occurred on the Near West Side since yesterday’s sunrise.

The victims in today’s update include an off-duty Chicago police detective, a high school repair contractor, three bicyclists who were targeted during an overnight spree, and a concealed carry holder who was shot at during a carjacking attempt.

Not bad for a weekday.

One robbery spree began around 6 a.m. Monday outside Chicago Bulls College Prep, 2040 West Adams.

A contractor was targeted as he unloaded tools to perform work at the school when a four-door sedan pulled up. Two men got out and took his tools.

Other robberies were soon reported in the 2100 block of South Leavitt, the 2100 block of South Western, and near Damen and Western.

An afternoon holdup spree began with an armed carjacking in the 600 block of North Wolcott around 4:45 p.m.

Another robbery occurred in the 1300 block of North Springfield about 30 minutes later.

Around the same time, an off-duty Chicago police detective was robbed at gunpoint in the 1000 block of North Trumbull, according to a CPD report. Three robbers confronted her on the street and robbed her of her bag.

Around 11:14 p.m. Monday, a gray car rolled up as a 33-year-old man was parking in the 1000 block of North Hermitage. Three people got out of the sedan with handguns, prompting the victim to flee the scene, a CPD spokesperson said.

The gunmen began shooting at the victim, but he escaped injury. His car was recovered at the scene, albeit with a flat tire. An individual familiar with the situation told CWBChicago that the victim is a concealed carry holder. He had his weapon at the time of the incident but decided to run rather than stop and try to return fire at two gunmen.

Then, an overnight spree began around 1 a.m. in the 2000 block of West Superior. Police said a 30-year-old woman was riding a bike when a car cut her off and forced her from the street. Three masked men got out of the car, robbed her at gunpoint of her phone and bag, then fled the scene. CPD said the woman suffered a “minor injury” but did not elaborate.

About five minutes later, three men exited a silver sedan to rob a 36-year-old man as he walked in the 1900 block of West Chicago Avenue. They pistol-whipped him, went through his pockets, and took his phone.

Another bicyclist was robbed at 1:49 a.m. in the 3000 block of West Armitage. A silver sedan forced the 32-year-old man off the road and three men emerged from the car to rob the bicyclist, police said.

A second bicyclist was targeted in exactly the same way on the same block at 1:58 a.m., according to a CPD media statement. That victim was a 30-year-old man, police said.

Finally, around 2:30 a.m., three men exited a silver sedan to rob a 53-year-old man as he walked in the 1500 block of North Milwaukee. Police said the robbers took his phone and wallet, then fled in the vehicle.

Back on July 21, Ald. Daniel La Spata (1st) told constituents in his weekly newsletter that Chicago police had hatched a “concrete and collaborative” plan to end the seemingly endless robbery sprees. But, while police have made a handful of arrests, CPD supervisors have also repeatedly ordered cops not to engage with carloads of armed robbers that are within their sight.

Late last week, La Spata told his constituents, “We will not see lasting results without addressing the root causes of violence with immediate and long-term investments.”

While the robbery sprees have been happening for months, here is some of our more recent coverage:

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CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets. Our editorial email address is