The city's restaurants have struggled to stay afloat as their indoor capacity remains limited and outdoor dining becomes less feasible as the weather cools.
Monday was a big day for Soulé Restaurant in West Town, as owner Bridget Flagg reopened for in person dining after months of take out only.
"We are trying to survive during this time because sales going down, we are trying to hold on to the customers," Flagg said.
The city of Chicago's 25% capacity rule for indoor dining means only a handful of tables can fit inside a tiny space.
Without a patio or sidewalk space, outside is not an option for Soulé like it is for many other restaurants.
"The industry is very concerned. Fifty-five percent of restaurant owners and operators here say they could see themselves closing in the next 6 months if things don't change," said Sam Toia, President & CEO IL Restaurant Association.
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To help keep some restaurants alive, the city is in the process of conducting a Winter Design Challenge.
Submissions have poured in an included all sorts of ideas from repurposing idle schools buses, igloos tents, to a floating device on the river.
Launched back in August, the challenge is all about finding ways for restaurants to stay open once the temperatures drop while still maintaining pandemic protocols to safeguard customers.
Architects, designers, servers and "foodies" have been submitting their plans with more than 643 entries in the contest, city officials said.
"There are definitely some good ideas, every little thing helps," Toia said.
Scott Weiner, the co-owner of several pizza places around Chicago, said most of the ideas are unrealistic.
"It cost nearly $10,000 to rent an igloo for seven to eight people, and that doesn't include heating, chairs and decor," Weiner said.
Instead of focusing on winter dining ideas, Weiner said the only solution for all restaurants, big and small, in every neighborhood is increasing in person dining capacity to 50%.
"I'm not looking at outdoor dining in the winter as a magic bullet, I really don't think it's going to push the envelope," he said.
Over the next few weeks, the submissions will be evaluated by a panel of local restaurants and community members. Following their review, the winners will be announced in October.
"Our restaurants and bars are the heart and soul of the city, and we must do everything possible to keep them operational during the harsh winter months," said Sam Toia, President and CEO of the Illinois Restaurant Association. "We need out-of-the-box thinking to address the hardship facing our industry. The Winter Design Challenge demonstrates the City's support of innovation in these trying times, and we look forward to ideas that are both creative and operationally attainable for our members."
Each winner will receive a $5,000 cash prize and opportunities to pilot their idea at restaurants and bars in the city.
Submissions can be viewed by visiting the IDEO Innovation Platform.