An 18-time convicted felon has added another conviction to his record after pleading guilty to burglarizing a luxury home on Chicago’s prestigious East Lake Shore Drive while the owners were asleep.
Robert Berry, 46, entered a residence in the 200 block of East Lake Shore Drive around 3 a.m. on August 19, 2025. This block is renowned for its upscale properties, including the iconic Drake Hotel and high-end co-op buildings. The targeted home had a listing price of $8.4 million.
Berry’s guilty plea resulted in a six-year prison sentence handed down by Judge Shelley Sutker-Dermer. However, he may be eligible for release after serving half of his sentence.
According to prosecutors, surveillance footage captured Berry sneaking into a rear gangway, scaling an eight-foot fence, and climbing a fire escape to access an upper-floor unit. The homeowners were unaware of his presence as he stole a purse containing $345. Subsequent video footage showed Berry leaving via the elevator and requesting an umbrella from the doorman as he departed. The stolen purse was later discovered by a building staff member on a stairwell landing.
Shortly after the burglary, Berry was apprehended in River North on a separate felony shoplifting charge. Police officers who recognized Berry from surveillance images of the East Lake Shore Drive burglary confirmed his identity and attire from the shoplifting arrest.
Berry claimed to officers that he believed he was being pursued on the night of the burglary, leading him to seek refuge in the gangway and ultimately gain entry through an unlocked door via the fire escape.
Public records reveal that Berry has been arrested in Chicago over 25 times since 2015, with convictions spanning from arson to theft, burglary, and drug-related offenses.
This incident underscores the ongoing challenges faced by law enforcement in dealing with repeat offenders like Berry. The case serves as a reminder of the importance of community vigilance and cooperation in combating crime.
