Chicago has been flying its rainbow flag for long enough to earn a reputation for being a gay destination. The Second City has historically crusaded for LGBTQ+ rights, with Illinois being the first state to repeal its sodomy law in the early '60s and the Chicago Gay Liberation movement kicking off not long after. During the '80s, the city launched its own LGBTQ+ international festival, and a gay men's chorus to boot. These days, it hosts the third largest pride festival in the U.S. (behind New York City's and San Francisco's) and is home to dozens and dozens of gay bars, not to mention all the gay bathhouses, lesbian coffee shops, and every other queer establishment in town.
Lakeview—better known as Boystown—is officially recognized as the oldest LGBTQ+ neighborhood in the country and it shows no signs of easing up on usage of the old rainbow flag anytime soon. A mile or so north of it is Andersonville, which was historically home to large Swedish and subsequently Middle Eastern populations but began gaining popularity with lesbians and gays back in the 1970s. It has remained one of Chicago's alternative community hubs ever since. Andersonville has everything from feminist bookstores to one of the country's oldest gay bathhouses (which is no longer open). You'll find hipster eateries and one of the most successful branches of the national gay burger restaurant and drinkery, Hamburger Mary's. Lately, gay pride has oozed into other parts of the city as well—notably Uptown, which now comprises countless gay bars, drag shows, and even a queer theater.
There's a vast selection of gay-friendly bars on the north side of Chicago, but it could be a jaunt for out-of-towners to get there, considering most of the hotel offerings are concentrated in the heart of the city. Thankfully, the Uptown area has broadened its horizons on the gay front, now possessing enough bars, clubs, and restaurants to be called an LGBTQ+ hangout (although still not as popular of a local gay hangout as Boystown). Some of the highlights include:
- Hamburger Mary's Brew & Grilles: This popular gay burger franchise is an inclusive and diverse hangout in the heart of Andersonville. This particular outpost of the nationwide chain also operates a craft nanobrewery that churns out some first-rate ales, including Mary Hoppins American Pale Ale and Leopold Belgian Dark Ale (plus lots of other rotating seasonal beers).
- Kit Kat Lounge: There's a high-end food and booze menu—plus a new drag show every half hour—at this Lakeview lounge.
- Big Chicks: Although not actually in either Lakeview or Andersonville, this endearingly fabulous gay bar is relatively close to both districts, in Chicago's ethnically diverse Uptown neighborhood. It boasts a sports-bar vibe that's welcoming for folks of all ages, gays and heteros alike.
- Green Mill: A prohibition-era Uptown cocktail lounge that serves up its old fashioneds with a side of live jazz.
- Jeffery Pub: This South Shore bar is a nice change in scenery from the same old Lakeview haunts. There's a different theme for nearly every night of the week.
- Cell Block: The atmosphere here is laid-back (think Wii and darts) save for Cell Block's famed leather-themed nights.
- The Closet: Come here for karaoke and chilled-out pregaming before hitting up Boystown's club scene.
- Roscoe's Tavern: In the summer, you'll find crowds gathering on Saturday afternoons on the patio at Roscoe's tavern.
When it comes to gay bars in Chicago, those of the club variety reign. The LGBTQ+ community here is certainly partial to fast-paced tunes, drag acts, and a dance floor. The gay club scene, specifically, is among the most thriving in the city, so after you finish off your happy hour beer and Proud Mary burger at Hamburger Mary's, make your way to one of these clubs to cut the rug until 4 a.m. Be prepared to pay a cover charge (cash, that is) to enter.
- Sidetrack: You can get drunk on slushies and sing along to show tunes all night long at Sidetrack.
- Berlin: A Lakeview hotspot that has a wild dance floor and drag performances from local celebrities. Everyday folks can join in on the drag competition, too.
- Scarlet Bar: It wouldn't be a gay club in Chicago if the dance floor wasn't complete with laser lights and a fog machine. Scarlet Bar in Lakeview is a vintage-inspired late-night hangout that has great early bird specials, too.
- Jackhammer: At the northern reaches of Andersonville, this rough, cruisy, and no-nonsense leather-and-bear haunt hasn't changed its old-school vibe to cater to a slicker, preppier bunch like other Lakeview bars have. This bar, offering a thunderous dance floor, presents a particularly beefy cadre of male dancers on Saturday and Sunday nights.
- Hydrate: This is where you go for a dance party at 4 a.m.
Much like it's a mecca for the LGBTQ+ community, Chicago is also a hotspot for stand-up comedy. In fact, The Second City is a world-famous, Chicago-based improv enterprise that has churned out class acts like Saturday Night Live's Cecily Strong and Josh Belushi and Glee's Jane Lynch. Naturally, there are a number of clubs and venues serving up queer-leaning comedy, including:
- The Annoyance Theater: Come here to see the beloved and locally famous improv group Baby Wine.
- The Laugh Factory: This widely recognized comedy venue regularly hosts gay-friendly acts like "The KIKI: Queer Comedy with Variety" and "Chicgaygo" in the past.
- Mary’s Attic: Upstairs from Hamburger Mary's is an attic bar that's been known to host a mean karaoke night and comedy show. In fact, Hamburger Mary's has its own weekly Mary's Comedy Club, held every Wednesday.
There are countless gay-friendly restaurants in the Windy City for your pre-drinks dinner (or your morning-after brunch, for that matter). Clark Street in Andersonville is a must-visit for quality food and cordial company and any eatery in Boystown is, of course, a good bet. Certainly don't miss:
- Chicago Diner: A vegan and vegetarian diner with an eccentric atmosphere in Boystown.
- Wood: Wood-fired American food (as the name suggests) and a world-class wine list and cocktail menu. This Boystown haunt is a perfect Saturday evening pregame.
- Tweet: For the morning when you wake up with a pounding headache and dry tongue, get your caffeine and pancake fix at Tweet, the biggest hangover hangout in Andersonville.
- Kanela Breakfast Club: Another local breakfast favorite in Lakeview.
- Beatnik On The River: A good alternative for folks staying Downtown, Beatnik On The River is a gay-friendly restaurant and bar that also has dancing.
On any given night, Chicago's LGBTQ+ crowd scatters to whatever bar, restaurant, or club is preferred, but on a few rare days of the year, they gather in a single place to wave their rainbow flags proudly. The biggest of the year is the Pride Festival, held on the last Sunday of June every year. This two-day block party attracts about 100,000 people per year. It features three stages for live music, 100 different merchant vendors, more food and drink than you could ever dream of, and a grand finale parade to top it all off. It's the third biggest pride event in the country. Also in June is Pachanga, which is basically a gay-friendly and Latin version of Chicago's famous Lollapalooza, but catered to a more alternative crew.
Other LGBTQ+ Events
The entire month of June calls for LGBTQ+-focused events throughout the city, including, aside from the Pride Festival itself, Andersonville Midsommarfest (a street fest rooted in Swedish traditions), the Proud to Run Half Marathon, Pride in the Park (a music festival in Grant Park), the Chicago Dyke March, and more. But, although Pride Month is officially the month of June, Chicagoans say pride is a year-long thing in their city. Additional events throughout the year include:
- Northalsted Market Days: This two-day party that takes over Boystown every August is the largest street fest in the Midwest.
- Reeling Film Festival: Chicago has such a robust LGBTQ+ community that it even has its own gay and lesbian film festival, which is held every September at various venues throughout the city.
- Pride Arts Center: If you're looking for something to do that doesn't involve eating or drinking in the Uptown area, then catch a queer show at the Pride Arts Center.
- Fabitat at Beauty Bar: Fabitat is what Beauty Bar calls an "LGBT extravaganza," featuring drag and DJ acts on a bi-weekly basis.
- Slo' Mo: Slo' Mo is a roaming party that plays "slow jams for the queer fam" at various bars around the city. Check the calendar for upcoming events.
Tips for Going Out in Chicago
- There is no state-set closing time, but bars with late-night licenses may only sell alcohol until 5 a.m. on Saturdays and 4 a.m. every other day of the week. In any case, the clubs tend to keep the party going late.
- Uptown establishments may be closer to most hotels, but they're likely to be more expensive than more low-key places in Lakeview and Andersonville.
- Gay bathhouses used to be abundant in Chicago, but these days, they've dwindled down to just one: Steamworks Chicago on North Halsted Street, which operates 24 hours a day and has for almost two decades.
- Gay-popular hotels in Boystown include Hotel Zachary, The Wheelhouse Hotel, City Suites Hotel, and Majestic Hotel. Wrigley Hostel is a more budget-friendly option.
- Consult Choose Chicago and GoPride's event calendars for LGBTQ+ things to do while you're in town.