[3] For many years, the parade was held only in Lake View East, a neighborhood enclave of the Lakeview community area.

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.

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).

Starting in 2013 the Chicago Pride Parade had reached over one million people each year, and the number continues to grow.

[8] The 2024 parade marched with a new start time, shorter route and 150 entries as the city sought to lessen its strain on various Chicago departments during a busy summer packed with other large-scale events, including the Democratic National Convention.

[9] The year 2019 marked the 19th Annual Pre-Parade Celebration, also known as Chicago's two day long Pride Festival.

Some of 2021's performers included Betty Who, LeAnn Rimes, Pabllo Vittar, Alex Newell and Inaya Day.