A number of city departments helped with the evacuation on Tuesday morning at the North Side hotel.
Some doors had to be broken down and a few residents were reluctant to leave.
The city says everyone has a new place to stay, although some have only found temporary housing.
This all started in 2007 when the city charged the Diplomat's owner, Jack Gore, with dozens of safety violations.
"This has been going on for over a year and a half. Mr. Gore has had ample time and money to have fixed it. He didn't. This is a result that didn't need to happen if he had acted diligently to fix the code violations," said Steven Quaintance McKenzie, Chicago Dept. of Law.
Gore has ignored our interview requests.
The case will be back in court next month and could go to trial this summer.