The Chicago Pride Parade is held on the last Sunday in June, so the weather is usually hot. The Pre Parade Celebration is just one of the many events held in Boystown in the month of June. Each year there are multiple different performers performing on the three main stages at the festival, some of this years performers included Betty Who, LeAnn Rimes, Pabllo Vittar, Alex Newell and Inaya Day. Saturday and Sunday prior to the Pride Parade. The hours of the Pride festival are 11 a.m. The streets are blocked off from traffic so the celebration can take place throughout the streets all weekend long. The festival is open rain or shine and each year it is held in Boystown, this year it was located on Halsted Street from Addison to Grace Street. Each year there is a suggested ten dollar donation while entering the festival for LGBTQ fundraisers, events, etc. 2019's Chicago Pride Festival saw over 100,000 people, the festival is held on the Saturday and Sunday before the Pride Parade. The year 2019 marked the 19th Annual Pre Parade Celebration, also known as Chicago's two day long Pride Festival.
Organizers aim for the event to return in 2022 with its original scheduling. Due to Delta variant, on September 3, 2021, the parade was cancelled once again due to COVID-19. The 2021 parade was postponed to October 3, 2021, in the hopes that an in-person parade could be held. The parade was cancelled in 2020 due to the COVID-19 pandemic. In October 2019, Richard Pfeiffer, director of the Parade since 1974, died. Starting in 2013 the Chicago Pride Parade has reached over one million people each year, and the number continues to grow. The 2011 parade included 250 entries and was attended by over 800,000 spectators, almost double the previous year, causing massive overcrowding and resulted in a reorganization of the parade route for the 2012 parade. Due to Chicago being one of the largest cities with a massive sports community, some other special guests have attended the Gay Pride Parade in Chicago, those include David Kopay (NFL running back), Billy Bean (major league outfielder) and Greg Louganis (Olympic diver). Sopel appeared in the parade to honor Brendan Burke, the gay son of the Maple Leafs' GM Brian Burke.
The 2010 parade featured an appearance from the Chicago Blackhawks' Brent Sopel and the Stanley Cup as part of the Chicago Gay Hockey Association's float. Among the entries were several marching bands, dance troupes, twirlers, and many political figures. On June 28, 2009, more than 500,000 spectators watched the 40th Annual Chicago Pride Parade. Both had strong support from many gay and lesbian voters. Both the Illinois Democratic and Republican parties have been heavily represented, most noticeably by former Governor Rod Blagojevich, a Democrat, and former Treasurer Judy Baar Topinka, a Republican. With the increasing political participation of gay, lesbian, bisexual and transgender Americans and the community's relatively high financial resources through political action groups and as individual donors, Illinois politicians have increased their presence at the Chicago Pride Parade. The parade then proceeds south on Broadway to Halsted, continues south on Halsted to Belmont, then east on Belmont to Broadway and finally south again on Broadway to Cannon Drive and Lincoln Park.
Recent parades have expanded their outreach (and ability to handle crowds) by extending the route into the Uptown neighborhood, beginning at the corner of Broadway and Montrose. For many years, the parade was held only in Lake View East, a neighborhood enclave of the Lakeview community area. The first parade was organized on Saturday, June 27, 1970, as a march from Washington Square Park ("Bughouse Square") to the Water Tower, but then many of the participants spontaneously marched on to the Civic Center (now Richard J.