Start with a visit to the popular Lakeview nightclub Roscoe’s Tavern. Roscoe’s books top queens nationwide, including Drag Race celebrities. And on Sunday evenings, head to nearby Charlie’s for Luc Ami’s open format show “QUEERIOD!,” a space for newer performers to develop their style and experiment in a “safe and affirming” crowd, says Cindy.

Drag in Chicago can also be found at brunches (Simone's is popular for their drag brunch), libraries, vintage shops, beaches, and parks. “Any time you can see drag outside of a club is always really fun,” says Cindy. These shows tend to be smaller and self-produced, providing intimacy for both performers and the audience. Cindy recommends keeping an eye on the social media of local drag acts, such as Irregular Girl, Neutral Gena, and drag collective Drag ‘N Drop, to find out about pop-up events.

The Northalsted area of Lakeview (formerly Boystown) is the city’s officially-designated gayborhood and a hot spot for LGBTQ+ nightlife. Here, some of Chicago’s oldest continuously existing LGBTQ+ bars, including Sidetrack and The Closet, bring regular crowds to rainbow-pylon–lined Halsted Street.

LGBTQ+ parties, pop-ups, and bars can be found throughout Chicago, especially in neighborhoods such as Andersonville, Logan Square, and Humboldt Park. A recent resurgence in lesbian-centered spaces and LGBTQ+ bars outside of the Northalsted strip offers even more options for non-cis and LGBTQ+ folks of color. Cindy’s picks include Black woman–owned bar Nobody’s Darling and lesbian cocktail lounge Dorothy, both known for their popular comedy, art, and music shows.

Like many cities, Chicago hosts a robust array of Pride events every June. Anchoring events include Pride Fest, a weekend festival in Northalsted featuring drag performances, concerts, food stalls, and a high-heels race; Chicago Pride Parade; Grant Park’s Pride in the Park; and Back Lot Bash, a women-focused outdoor music festival in Andersonville. Pride South Side also hosts an annual festival as part of Chicago Black Pride, featuring a variety of LGBTQ+ events at locations across the city.

Outside of Pride Month, Market Days is a longstanding LGBTQ+ festival held in Northalsted every August. Cindy also recommends checking out Chicago’s museums like the Adler Planetarium for special Pride-themed evenings with after-hours viewings, drinks, and performances.

For Cindy, a trained theater artist, a visit to one of Chicago’s theaters is a must-do. About Face Theater, First Floor Theater, and Free Street Theater are three companies that “put queer stories at the forefront,” despite not being specifically LGBTQ+ associated.

Cindy’s other must-dos include a visit to the Gerber/Hart Library and Archives, where you can learn more about the city’s LGBTQ+ history, and the National Museum of Mexican Art for a glimpse of Latinx, Chicano, and Mexican culture. For time outside, Kathy Osterman Beach in Edgewater is a popular LGBTQ+ hangout—don’t forget to snap a photo with the rainbow pier—while Logan Square Park is a lounge-worthy spot popular with locals.

For this Latine queen, the best food spots can be found in the city’s Mexican neighborhoods, around Logan Square, Pilsen, and Little Village. For late-night tacos after a wild evening of drag, try Raymond’s or El Taconazo El Tio. If you’re after hearty portions at an affordable price, head to Logan Square’s El Cid or one of the branches of Taqueria El Milagro.

According to Cindy, lovers of green space and nature should stay around Hyde Park to enjoy easy access to Promontory Point, several beaches, and the vast expanse of Washington Park. Logan Square’s many LGBTQ+-friendly restaurants and bars makes it perfect for travelers looking for laid-back vibes and an active nightlife, while North Side neighborhoods Andersonville and Northalsted boast a large concentration of LGBTQ+ businesses, shopping, bars, and nightlife.