Boarded up windows and doors could be seen downtown Thursday.
"As we know, this city has a poor track record when it comes to protecting businesses," said Scott Shapiro, owner of Syd Jerome.
The looming unknowns ahead of next week's convention are why Shapiro said he knew he had to take precautions to keep his decades-old business safe.
"We felt it was more prudent to board up, since our customers and their employers have told them to stay home throughout the convention for their own safety," Shapiro said.
That's why his downtown storefront at Syd Jerome on Clark Street is shielded by plywood, as thousands of protesters plan to descend on Chicago for the DNC.
His store was looted during civil unrest in 2020.
And back then, he didn't take down the plywood until more than a year later.
Now, it's back up in fear of history repeating itself.
Chicago DNC 2024: Live updates on street closures, parking, protests and more
"The peaceful protesters, the scheduled protesters, we're never worried about. It's the people that embed themselves and take advantage of those protests for their own agenda that we worry about," Shapiro said.
Other downtown businesses are also taking precautions, like the Garland Building on North Wabash Avenue and Washington Street, which houses multiple office spaces, stores and restaurants. Chicago Board-Up Services has been quite busy.
"We're boarding them up tight, so that there's no entry," said Vicki Fichter, owner of Chicago Board-Up Services.
Fichter said her crews have already boarded up more than a dozen businesses, and received over 40 calls for work, mainly in the West Loop, downtown and around the Daley Center.
But, she said, work being done during the convention could be difficult to complete.
"If things do arise and streets may be shut down, we can't get to you," Fichter said. "So, if they want to prevent it and have it done ahead of time, we are telling them that we prefer we get done now."
With those concerns, Chicago police are remaining on-guard, in case protests go awry.
"The First Amendment protections does not include rioting; it doesn't include criminal acts. It doesn't include breaking the law. It doesn't include violence, vandalism, those things that we are not going to tolerate in our city," CPD Superintendent Larry Snelling said.
Many owners say their storefronts will remain boarded up until the convention is over, but are hoping they could take it down much sooner.