Chicago is quite a liberal city, especially for the Midwest. There is a thriving GLBT community there, with a neighborhood affectionately known as "Boystown" (Lakeview) and another neighborhood with a both large lesbian and gay male populations,  Andersonville. The city even constructed large structures with rainbow colors on them along Halsted Street, which runs through the Boystown neighborhood. Obviously, gays and lesbians live in many other Chicago neighborhoods, but these two neighborhoods have especially concentrated GLBT populations and the businesses cater to them.

Some of the most popular gay bars in Chicago include: Spin , SideTrack , Roscoe's, Cocktail, Hydrate , and Berlin , which are all located in the Boystown neighborhood. Crew  and Big Chick's  are also very popular, and are located in Chicago's Uptown neighborhood, which many are now referring to as "Boystown North."  Stargaze has a mostly lesbian clientele, and is located in Chicago's Andersonville neighborhood. Gentry , Chicago's premier cabaret bar has two locations, one downtown, and one in Boystown.