Concrete barriers positioned on streets in the Gold Coast were among the resources deployed by the city during the drill.
The drill came after city officials assured business leaders on a conference call that a plan is in place to guard against future looting, but some business owners remain skeptical.
"I'm glad to see that they're now taking it seriously, and they're starting to deploy resources to address the issue," said Scott Shapiro. He owns the Syd Jerome clothing store in the Loop that was hit by both rounds of looting. His store windows are still covered up.
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"As far as the city instilling confidence in its residents and its merchants, I'd have to give it a failing grade," Shapiro said.
Amid that backdrop, the city's Office of Emergency Management and Communications conducted the exercise Thursday night. The downtown-wide drill took place in the area bounded by Division Street on the north, 18th Street on the south, Clark Street on the west and Lake Shore Drive on the east.
Though officials won't tip their hand, multiple Gold Coast business owners told ABC7 that they were told the drill, in part, involved coordination of pre-positioned police and city vehicles to rapidly block traffic in and out of retail areas, perhaps in response to the use of car caravans by looters.
Alderman Brian Hopkins said after two rounds of looting this summer, the city has improved its response with support from state and federal agencies.
"We are prepared, unlike the weekend of August 10, when we were completely caught off guard," Hopkins said. "Now there's training in place, and the officers in the field will know exactly what to do instead of scrambling in a chaotic environment which is what recently happened."
The city said the drill had been planned for weeks and is not in response to the events in Kenosha or this Saturday's Black Lives Matter march and rally, which aims to shut down the Mag Mile.
But stores like Canada Goose off the Mag Mile are preparing regardless, especially in light of the protests and riots in Kenosha.
Joe Downey with Crane Construction boarded up the luxury outerwear shop that remains empty. Downey said the city hasn't been prepared.
"In my opinion, they let it go too long," he said.
Squad cars could be seen in front of boarded-up storefronts for high-end, luxury retailers like Gucci, Tiffany and Cartier. Some shops in the area have been boarded up since destruction and looting a few weeks ago.
Many downtown businesses took part in a call with city leaders Thursday to reassure them of security plans for the weekend. Based on that call, Steven Hartenstein said he's planning on business as usual at Tavern on Rush.
"We feel very comfortable, not planning on boarding up," he said.
Gold Coast Bentley had damage and looting, and they think the drill will help.
"I think it's good for the people with the businesses," said George Chiarelli of Gold Coast Bentley. "We need police protection. We need police action."
Adam Skaf, spokesman for the Magnificent Mile Association, agreed.
"If something goes awry this weekend, it could spell disaster for some downtown businesses," he said.
Chicago police said they're prepared for multiple demonstrations planned for this weekend and plan to detail their safety plan during a news conference Friday morning.