Summer in Chicago can be fickle, the weather can often be chilly, and it has been known to snow up until late May.
However, it can also be 80 degrees the next day. While in most parts of the country, Memorial Day is the unofficial start of summer, in Chicago, it’s the unofficial start of Pride, as it’s also International Mr. Leather (IML) Weekend which took place this year May 23-27. For more information, go to imrl.com.
Of course, while in town you must hit the gayborhoods, yes plural. There’s the neighborhood with all the bars, which used to be called BoysTown until someone got their knickers in a twist, so now it goes by its semi-official designation NortHalsted (because it’s the north end of Halsted, the longest street in the city, for you size queens out there). In the 1970s and ‘80s, it was also where the much of the LGBTQ community lived until we got priced out. But the bar and club owners were smart. They bought their properties and so Halsted Street remains an LGBTQ entertainment district. It is roughly the same length as Wilton Drive, just short of a mile, with about the same number of bars, clubs, and restaurants lining it.
While you’re there, check out the Legacy Project. Chicago likes to call itself “A City of Neighborhoods” and designates them with public art. When the area surrounding Halsted Street was primarily home to the LGBTQ community, the city erected rainbow pylons. Local activists petitioned the city to allow them to adorn them with bronze plaques of LGBTQ pioneers and now, it’s the world’s largest outdoor LGBTQ Museum!
Here are the bars you want to check out on Halsted (and a couple in the surrounding neighborhood) as you stroll along the Legacy Walk. At the corner of Roscoe and Halsted, are a trio of bars that form the anchor of the neighborhood. Sidetrack, jokingly referred to as the bar that ate Halsted, is the longest-running, now in its fourth decade. It started as a little storefront and kept adding adjoining spaces. It now covers half a block and features eight bars, including a rooftop deck. Sidetrack has been named the best LGBTQ bar in the world numerous times and is beloved by the community. It was the city’s first video bar and pioneered its own version of show tune videos, a la Rocky Horror, where patrons yell back and have pre-set bits that can go on for 15 minutes. Friday cocktail hour, Sunday afternoon, and Monday nights are when you can catch these shows. Roscoe’s, second only to Sidetrack in longevity is a little more laid back. Karaoke is popular and there’s a restaurant serving up everything from salads and burgers to bar snacks. Drag shows are big, especially drag bingo and brunch. And the dance floor can get packed. Progress Bar has prime street-watching window seats and has a distinctly different feel day and night.
Heading south on the Halsted Strip, there are several popular restaurants, as well as Splash where drag queens dominate the scene, D.S. Tequila, which is as much about the drink as the food, Scarlet where DJs and drink specials fuel the early bar and late-night lounge scene and at the end of the gay section of Halsted is Lucky Horseshoe, where multiple rooms with stages feature male strippers every night.
Heading north from Roscoe and Halsted, you’ll come upon Replay, with vintage video games, beer and bourbon, Elixir Lakeview, small plates, and sophisticated bar snacks with high-end cocktails, Hydrate, for shows, music, dancing, and late-night parties. Cross Addison, and walking past the Town Hall Apartments, the LGBTQ Senior Housing development that incorporated the former police station many LGBTQ folks were taken after bar raids in the “bad old days,” and you’ll come to Bobby Love’s, which has cheap drinks, piano bar and karaoke, Kit Kat Lounge, for cocktails or dinner and drag show, Cell Block, a leather bar with pool, darts, theme nights and drink specials, Fantasy Nightclub, the biggest nightclub on Halsted, and The North End, near the north end of Halsted and a neighborhood hangout since 1983!
Halsted ends where it intersects with Broadway, an angle street that also used to be a nexus of LGBTQ nightlife. Just turn the corner and you’re at Charlie’s, a Western-themed dance club with drag shows, karaoke, bingo and late-night hours. A few blocks further down you’ll come upon The Closet, opened in 1978, this tiny, neighborhood bar is friendly and with a largely women clientele, but it is very male-friendly. Farther West, on Clark St. you’ll find Shakers on Clark, a sports bar, and Smart Bar, where the club kids have been going for decades.
Our second LGBTQ community is Andersonville, a few miles farther north in the city. If Halsted was known as Boystown, then this neighborhood was nicknamed “Mandersonville” because many older gay men bought condos here because they were larger, more expensive (and expansive) or sometimes “Lesbiana Shores” because of its proximity to the lakefront and the fact that many lesbians moved here because of the low crime rate. The neighborhood has also retained its European charm, but now with more of an international flair, there are restaurants of nearly every cuisine in the world and the bars tend to be more laid back.
Marty’s Martini Bar is a tiny upscale lounge, SoFlo Lounge is geared toward bears as their events may indicate (GRRR, DILF, Bearaoke, Nerd Bear Trivia), Elixr-Andersonville offers high-end cocktails, Meeting House Tavern has a night for everyone, Nobody’s Darling, is a popular women’s lounge, and Atmosphere is the neighborhood’s dance club.
There are many Andersonville-adjacent bars and clubs. In Uptown, Big Chicks attracts a diverse crowd, The Baton Show Lounge is a famous drag show bar, and there’s also 2Bears Tavern. Farther north in North Edgewater/Rogers Park, you’ll find Whiskey Girl Tavern, Jarvis Square Tavern, R Public House, Little Bar Wolf, the gay rock and roll bar, Jackhammer, The Glenwood, Rogers Park Social, and Chicago’s oldest leather bar, Touché.
In other neighborhoods, not adjacent to the northside lakefront, you’ll find Second Story Bar (off Michigan Avenue), the West Loop’s drag dinner theater Lips. On the South Side there’s Jeffrey Pub, Chicago’s oldest LGBTQ bar, and in Hyde Park, Club Escape. Other neighborhood bars include La Cueva in Little Village, Dorothy (West Town’s ‘70s-inspired subterranean lesbian cocktail lounge), and Inn Exile (near Midway Airport).
A city is more than its bars. You need to check out some of the festivals and landmarks. For Chicago’s most well-known landmarks such as Cloud Gate (aka The Bean), you can get that info anywhere. Here’s some good queer stuff you’ll want to explore.
The Leather Archives & Museum celebrates the history of fetish culture and the queer community and remains the only institution in the country dedicated to the compilation, preservation, and maintenance of alternative sex culture. Take a self-guided tour through eight fascinating exhibition galleries, including the Dungeon, featuring S&M and bondage equipment, a leather bar diorama, a leather history timeline, a guest artist gallery, and 20 murals by the celebrated erotic artist Etienne.
Gerber/Hart Library and Archives is the Midwest’s largest LGBTQ+ circulating library, with over 14,000 volumes, 800 periodical titles, and 100 archival collections. The library’s progressive exhibits cover everything from Chicago’s drag revolutionaries to a collection of Pride memorabilia. Guided tours of the library are available.
See Chicago like a local, with a local, with free Chicago Greeter walking tours. Led by the people who know the city inside and out, you’ll explore authentic Chicago. The tours can be customized to focus on special-interest areas such as architecture, foodie culture, and, of course, LGBTQ+ Chicago, in the language of your choice.
Perhaps to compensate for its long winters, during the summer there is at least one neighborhood festival going on every weekend, many of them queer-focused or at least with a major queer presence. Here are some to check out.
Navy Pier Pride: city-sponsored full day of family-friendly festivities in honor of the LGBTQ community, includes story time with drag queens and live performances.
Pitchfork Music Festival: while not specifically LGBTQ, has a queer vibe and features alternative music acts. (July 19-21.)
Fireworks: Chicago’s fireworks display for Independence Day is spectacular. Chicago and the suburbs up and down the lakefront set off the fireworks from the lake, so the best place to see them is from the lakefront. Avoid going downtown as the crowds are crazy. Instead head toward any of the promontory parks that jut out into the lake, or better yet, strike up a friendship with someone who lives in a high-rise along the lake and sip your martini in air-conditioned (and bug-free) comfort while you enjoy the sights. This might also be a good time to visit The LGBTQ Community Center on Halsted and stop on its rooftop observation deck.
NortHalsted Market Days: one of the biggest street fests in the country. It’s all about life and community in Chicago’s LGBTQ hood. The event includes live music on five stages, DJs and dancing, vendors, food, and men wearing as little as possible. And it only seems like every gay person in the Midwest is there. This event attracts more than a million people to Halsted Street. (Aug. 10-11.)
Miss Continental International: Labor Day marks the end of summer and is also the weekend of the Grande Dame of drag beauty pageants. (Sept.1-2.)
The Reeling LGBTQ+ Film Festival is the second longest-running LGBTQ+ film festival in the world. (Sept. 19-Oct 6.)
Chicago LGBTQ Hall of Fame (HoF) Annual Induction Ceremony: The days grow colder, but the season doesn’t officially close until the HoF holds its event at The Chicago History Museum. The HoF is the only city-sanction LGBTQ hall of fame in the world. Each year anyone in the community can nominate an individual, business, or organization, for inclusion or as an ally, designated a “Friend of the Community.” Members of the HoF then meet to evaluate the nominees. Those who are deemed worthy are inducted in a ceremony traditionally presided over by the city’s mayor. The event is open to the public and includes a reception beforehand. (Oct. 1.)
For a guide to events and dining check out the monthly in-print Grab! Magazine or online Windy City Times LGBTQ publications.
