Although Chicago has among the greatest selection of gay nightspots in the country, the majority of these hangouts - from bars and discos to LGBT-popular restaurants - are in popular mixed residential-commercial neighborhoods on the north side of the city. You can find extensive lists of establishments in the Chicago Lakeview Gay Nightlife Guide and the Chicago Andersonville Gay Nightlife Guide. These neighborhoods are a lot of fun, but they're also a bit of a haul - by cab or public transit - from downtown Chicago, which is where most of the city's hotels are.
Fortunately, there are a couple of very fun gay nightspots right in the heart of downtown, not to mention an almost endless supply of terrific restaurants, many of them with mixed gay/straight followings. Additionally, on the city's South Side, you'll find a pair of gay bars that cater predominantly to African-American patrons, Club Escape and Jeffery Pub. It's also a bit of a distance to reach these bars,... but they're both legendary nightspots that are well-worth checking out, especially given that many of the nation's gay African-American hangouts have steadily disappeared over the years.
Here's a more in-depth look at these Downtown and South Side Chicago gay social establishments. Also take a look at the Chicago Gay Bathhouse and Sex Club Guide, which has plenty of advice on where to meet guys looking to hookup around Chicago.
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Club Escape, South Side - gay bar
Set behind its restored art deco facade, Club Escape (1530 E. 75th St., 773-667-6454) is one of two long-running gay bars on Chicago's Southside, catering largely to the city's sizable African-American GLBT crowd (the other is the Jeffrey Pub). Escape is most popular on weekends, when it hosts some of the top drag acts in town. Thursday's "Ladies Night" is also well-attended. During the week it's a mellow scene, but $10 pitchers of beer and a friendly staff keep keep regulars coming back.
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Brian's Speakeasy, Downtown - gay bar
The Near North space at 440 State Street, which was for years the Gentry gay bar and then Lady Luck and Downtown Bar and Lounge, is now Brian's Speakeasy (440 State St., 312-464-1400). It's a welcoming spot that's quickly become popular with both suits after work, and tourists staying at the dozens of hotels within a short walk, including Kimpton's gay-popular Hotel Palomar Chicago, which is diagonally across the street. The CTA Red Line's Grand stop is just a block away, too.
Brian's has a great happy hour and an impressive cocktail list, not to mention quite a few high-quality wines by the glass and beers on tap. There are two very attractive spaces - the larger one, as you enter, with music and a bit more energy, and a quieter, sophisticated little lounge to the right that's better for conversation. It's a great space with a hip, central location, and it's terrific that new owners are keeping the longtime destination for downtown Chicago gays and... lesbians alive and well.
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Jeffery Pub, South Side - gay bar
One of the most historic gay bars in Chicago, Jeffery Pub (7041 S. Jeffery Blvd., 773-363-8555) opened on this city's South Shore more than 40 years ago and has been ground zero for the city's African-American gay community ever since. The venerable bar hosts drag shows and has dancing throughout the weekend - there's a somewhat cramped dance floor, but the music's great and the energy high.
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Baton Show Lounge, Downtown - gay bar
One of the longest-running gay clubs in the Midwest, the quite fabulous Baton Show Lounge is also one of the country's most illustrious female impersonation cabarets. It's also one of only a few Chicago gay establishments downtown (in the Near North neighborhood, at 436 N. Clark St., 312-644-5269). The dishy, diva-packed drag shows are held Wednesday through Sunday, three times nightly, beginning at 8:30 pm - it's a good idea, especially on weekends, to make a reservation.