It included multiple viewing locations with screens and concessions across Millennium Park and a main stage on the Great Lawn with the traditional tree lighting ceremony.
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It was followed by fireworks and a special concert headlined by singer-songwriter Brian McKnight.
SEE ALSO | Chicago's official Christmas tree revealed
The ceremony was virtual last year because of the pandemic, but Chicago's Black Santa "Dreezy Claus" was on hand with a festive mood.
"The fact that I'm probably the only or the first one of color to be Santa Claus in the history, 108 years of this, it's huge," Dreezy Claus said.
Instead of confining the celebration to a limited space, the re-imagined event featured a main stage on the Great Lawn along with multiple jumbo screens, where event goers can view the festivities from a number of locations. It's all in an effort to keep everyone safe.
"We wanted to make sure that people had the chance to spread out but also to enhance the experience," said Deputy Commissioner Nancy Villafranca-Guzman, Chicago Office of Cultural Affairs & Special Events.
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And even with Friday night's performances and entertainment, the 51-foot blue spruce donated by Chicago's Benavides family from the Logan Square neighborhood remains the star.
Covered with some 53,000 Christmas lights, the city's official Christmas tree is the reason most are here.
Cara Groman and her relatives drove in from Ohio to begin celebrating the holiday Chicago-style.
"My niece is marching in the holiday parade from Whitehouse, Ohio tomorrow night, so this is kind of our first time out and about since COVID started," Groman said.
Another sign that the holiday season is here is the return of the Christkindlmarket. Many warmed up with some fried schnitzel and hot spiced wine.
"It's really festive. I feels like we're back to normal. It's so nice to have like a fun vibe around and getting in the Christmas spirit," said Suzi Lilley.
"It's a time, an event for family to spend time together and like make those memories and be together, enjoy each others' company," said Morgan Miller.
Skating at the McCormick Tribune ice rink is also back. The skating is free and online reservations are required.
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College student William Ellis was one of the first people on the ice.
"It's awesome that everything is finally coming back," Ellis said. "I missed the holidays."
And as Chicago's Christmas tree lights up, for many, so do holiday wishes.
"Happy holidays and I hope they get to spend it with who they love!" McKenna Cravle said.
The holiday celebrations also spread out of the city. Aurora's Winter Lights Celebration warmed the hearts of downtown Aurora.