"Very hard. It's very hard this summer. It's very hard. It's not easy to do it with COVID, you know," owner Milton Garfias said.
Garfias fears it'll only get harder with cooler weather forcing guests indoors, where he can only seat six tables.
"Sometimes I can't sleep because I'm thinking the bills," he said. "I'm thinking of my employees, you know, and everything."
Garfias is far from alone. An estimated 86% of restaurant owners report they won't make a profit in 2020 and average revenue is down 50 to 70 percent from a year ago.
The Illinois Restaurant Association has been lobbying the city of Chicago to raise indoor dining capacity from 25% to 50%, but that may not be enough to help some owners.
"You're more likely to catch the coronavirus in your buddy's basement than you are in a restaurant here in Chicago," said Sam Toia, of the Illinois Restaurant Association.
In fact, those home gatherings - including backyard cook-outs with family and friends - are now a main driver of infection.
"What we recommend people do is that at the beginning of the gathering or when the gathering is planned, we sort of announce the rules," said Dr. Mark Loafman, Chair of Family Medicine, Cook County Health. "We're going to keep ourselves six feet apart. When we can't be, we're going to wear masks. We're going to wash our hands before and after the meal."
The Boka Restaurant Group - which owns several well-known eateries, including The Girl and the Goat - informed the state this week of its intention to lay off more than 500 workers.
"I don't see in my lifetime, any period of time, that could be considered more challenging than right now," said Doug Roth, a restaurant consultant at Playground Hospitality.
Roth said research shows more than 70% of diners have concerns about eating indoors. He thinks local governments should invest in heaters, tents, and other setups to maintain outdoor dining on closed streets.
"We need something at this point that's going to help carry us over in what has historically been the most important quarter for restaurants or retail, which is the fourth quarter," Roth said.
Roth said it will be vital for restaurants to have a strong take-out and delivery strategy for the colder months.
As for eating outside in the fall and winter, there's a new mantra that we're hearing: BYOB, or Bring Your Own Blanket.