An 18-time convicted felon is now accused of scaling more than 10 floors to burglarize one of Chicago’s most exclusive private homes while the owners were asleep.
Prosecutors say 46-year-old Robert Berry entered a residence in the 200 block of East Lake Shore Drive around 3 a.m. on August 19, 2025. The block, which includes the landmark Drake Hotel and a row of early 20th-century luxury co-ops, is one of the most expensive stretches of real estate in the city. The victims’ home was recently on the market for $8.4 million.
Video allegedly captured Berry slipping into a rear gangway, climbing an eight-foot fence, and then scaling a fire escape to reach the victim’s home on the upper floors of the building. The residents were asleep when Berry entered and took a purse containing $345, according to prosecutors. They said surveillance footage later showed him taking an elevator down from the upper floors and asking the doorman for an umbrella on his way out. The doorman obliged…