Man charged with armed home invasion in River North has been arrested 5 times since September

Omari Bailey is seen in mugshots from September, November, December, April 23, and April 28. (Chicago Police Department, Cook County Sheriff’s Office)

CHICAGO — A man charged with committing an armed home invasion in River North over the weekend has been arrested four other times since late September, including just last week, according to court and Chicago police records.

Those court records also show that prosecutors dropped the first three cases, even though Omari Bailey didn’t even show up for court in two of them.

A couple living in the 700 block of North Hudson called 911 around 1:30 a.m. Sunday after the 18-year-old entered their unit without permission and walked into their bedroom with a knife, police and prosecutors said.

The couple locked themselves in their bedroom while they waited for the police. Meanwhile, Bailey went through their unit, collecting property, court records say.

A doorman met police at the building entrance and let them into the couple’s apartment. Police allegedly found Bailey standing in the kitchen area, holding the victims’ property and the knife.

The victims, a 28-year-old man and a 30-year-old woman, confirmed that Bailey was the man who walked into their bedroom earlier, police said.

He is charged with two counts of armed home invasion, two counts of armed robbery, two counts of burglary, and unlawful use of a knife. Judge Charles Beach detained him until his next court date, May 6.

Chicago Police Department arrest records show Bailey was arrested in the Loop at noon on April 23 for aggravated assault with a deadly weapon. He was released from the station, and the case details hadn’t even been entered into the court clerk database as of Monday.

Bailey’s first adult arrest in Chicago was for misdemeanor battery on September 23. Records show that he did not show up for his October 16 court date, but prosecutors dropped the case anyway.

He was arrested for retail theft on November 15. Once again, he didn’t show up for court on December 8. And, once again, prosecutors dropped the case without his presence.

On December 9, he was arrested for aggravated assault with a deadly weapon. That time, a judge put him on an ankle monitor. He showed up for his court dates that time. Prosecutors still dropped the case three weeks later.

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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