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"It makes me more aware of my community, the struggles we went through and the struggles we're still going through," said Dante Hall, resident.
Friday the rainbow flags went up along Halsted Street. The streets themselves are painted, the rainbow of colors reflecting the mood of the neighborhood.
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Friday night, Center on Halsted held a party to kick off the weekend of celebration.
"It's incredible to think that we've moved so far. I'm proud, and I'm happy, proud of Chicago," said Laura Ustryski, who was attending the celebration.
In Grant Park, crews set up the stage for Saturday's first ever Pride in the Park, a start-studded concert headlined by Iggy Azalea.
But the main event is Sunday's parade.
"Everyone is so happy," said Andrea Fogarty, who will be attending her second pride parade. "And I think that's the unique thing about the pride parade and festival. Everyone is just there to be loving and fun. You just want to be together and around people. We love it."
The 50-year touchstone of this year's parade refers to 1969, when police raided the Stonewall Inn in New York City. The subsequent uprising was a catalyst for the modern pride and LGBTQ equality movements, a transformative historical moment still present today. It imbues the parade with so much meaning.
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Jim Flint recalled being gay in Chicago in the 1960s, and said at that time it could land you in jail. While working at gay bars he was arrested multiple times.
"If a vice officer would walk in, and he would buy somebody a drink, then it's soliciting for prostitution. It was just every drummed up charge they could," Flint, who owns Baton Show Lounge, recalled.
Flint will serve as a legacy grand marshal of the parade. Mayor Lori Lightfoot, Chicago's first openly gay mayor, also serves as this year's grand marshal.
"I am so proud that we have six gay aldermen," Flint said. "We have state representatives. We have judges. We have people in the sanitary district. I'm just so proud of our community."
About 1 million people are expected to attend, and folks are encouraged to take public transportation to the event.
"For me, it was like a coming-of-age type thing," Hall said. "When I went to Pride, I felt an embrace of being who I can be as myself in a safe community, a safe environment."
Whether it's their first parade or they've attended year after year, the pride parade is special, and very personal, for so many.
"I live in Ohio now but I'm back for the weekend, so I can't wait to actually experience it for the first time. I hear it's just a big celebration of love and excitement," said Grace Grannan.
"This is the one time where there is an area for us be in one place and not be judged," said Cat D.
"What Pride means to me is self-love and respect. And everyone coming together as a whole," said Kevin Emanuel.