This year, concerns about COVID-19 mean the show must not go on.
The city has cancelled all major summer events through Labor Day, including the Chicago Air and Water Show and the Taste of Chicago.
At Art of Pizza on State Street the loss of summer festivals cuts deep.
"It's upsetting. It's upsetting. We're going to probably have a lot less traffic come the summer time. I'm pretty sure it's going to be the same thing for the whole neighborhood," said Danny Drinkwater of Art of Pizza.
Art of Pizza among the thousands of businesses that normally get a slice of the hundreds of millions of dollars generated by Lollapooza, Taste of Chicago, the Air & Water Show, Jazz Fest and more.
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"Well, it's disappointing, but it's for the safety of everybody, so it's just something we have to get through this year," said Tony Karamuzis.
Lollapalooza had been set to take place in Grant Park from July 20-August 2, but it will not be taking place with fans in attendance due to COVID-19 concerns.
Mayor Lori Lightfoot emphasized the potential risk of COVID-19 spreading during her press conference Tuesday.
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"Bringing that many people from all over the country downtown in Grant Park every single day, we might as well light ourselves on fire," she said.
DCASE said, "Lollapalooza will honor its annual summer tradition by bringing Chicago, and the world, together around a common bond of community, civic engagement and, of course, live music in a weekend-long livestream event July 30-August 2."
Further details are expected to be released next month, DCASE said.
RELATED: Chicago city events including Taste of Chicago, Air and Water Show, Jazz Fest canceled through Labor Day
The events are more than just cultural staples. The are also economic pillars that bring in hundreds of millions of dollars to the area.
"There are thousands of businesses that depend on these festivals for their livelihood," said Laurence Msall, president of the Civic Federation.
Msall said along with the city's announcement of a projected $700 million budget shortfall due to the virus shutdown, the loss of revenue from festivals adds to need for more federal funding.
"It's not just Chicago. It's not just the Midwest. It's all around the United States, needs revenue support," Msall said.
Though the festivals are a no-go, the city is planning virtual gatherings centered around food, music, and dance.
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The Taste of Chicago will be re-imagined as "Taste of Chicago To-GO" which will have a community eats program supporting 25 neighborhood restaurants and food trucks providing free meals to non-profits serving healthcare and other frontline workers, the city says.
"Imagine tens of thousands of people across the city dancing, line dancing and house music and salsa, everyone going at it and then sharing what they're doing, and a communal spirit comes out of it," said Commissioner Mark Kelly from the Chicago Department of Cultural Affairs & Special Events.
Other events that have been cancelled include Chicago SummerDance, the Chicago Jazz Festival and a majority of the programming at the Chicago Riverwalk.
"We must provide ways for people to enjoy the spirit of a Chicago summer while prioritizing health and safety," said Mayor Lightfoot. "As difficult as it is to remove these in-person events from our calendar, we are pulling out all the stops for an inventive, engaging and fun festival season this summer."
The mayor has yet to announce a date for reopening of either the Riverwalk or the lakefront.
"I hope to be able to open the lakefront as soon as possible," she said. "I'm pressing my folks to finalize a plan... I'm anxious to make an announcement about reopening the lakefront."
Lightfoot said she was also looking at allowing the restaurants on the Riverwalk to reopen consistent with the overall guidance that other restaurants have been given.
With the loss of revenue, the city now faces tough choices.
Mayor Lightfoot said property tax increases and city layoffs are not off the table.