Gay Pride Weekend, Chicago also see: night chicago | chicago night 2 | bike chicago | chicago 12.05 | chicago 12.06 All images by Mark File. Please do not copy without permission. (2007) More than 400,000 people participate in or watch Chicago's Pride Parade, held on the last Sunday in June. The parade is three hours long and covers several miles through Boystown. The celebration also includes the PrideFest street fair on Saturday. Read more. The party goes all weekend! For the most fun, go to my favorite bar (and the most popular gay bar in the country), SideTrack. Sunday nights at this sprawling video bar feature "singalongs" with videos of broadway and movie musicals. What a blast! Visit the new Center on Halsted, the nation's largest center for the LGBT community. Wave it Tom! THANKS to fun friends for making a very memorable celebration: Tom (above two rows, waving flag), Ray (orange cap), the Chicago gang that I met last winter (birthday boy is getting a spanking!), Rob (below left) and Richard (below right).