Best Gay And Lesbian Hotspots in Chicago

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Alan Schin
Updated on August 06, 2025 | 12 min read
Best Gay And Lesbian Hotspots in Chicago

The Windy City has various locations where queer folks can gather to party. Whether you want a pub with a laid back vibe, a classy restaurant, or a night club with beats pumping all night long – you’ll find it in Chicago. You can catch a queer-friendly comedy show, see some live music, or challenge your friends at drag bingo. There’s just no place like Second City. So, make your way to the Loop, Andersonville, Uptown, or the Magnificient Mile. We’ve got the line on the best LGBTQ+ events and nightspots Chicago has to offer.

Top 10 Gay Bars And Clubs in Chicago

North Halstead or Boystown is the prime LGBTQ neighborhood in the windy city, and that is where most of the best gay and lesbian bars are going to be found in the area. Let’s take a look at some of the best bars at various locations in Chicago.

1. Bobby Love’s

Halstead or Boystown is the prime LGBTQ community and neighborhood, and that is where you can find all of the best gay and lesbian bars in the city of Chicago. Bobby Love’s is no exception to this rule. If you’re looking for a gay bar with less of a club atmosphere and more of a cozy and relaxed place to go then this is the place for you. Here you don’t have to worry about clubbing or dance parties. All you have to do is sit, have some drinks, sing karaoke, and just hang out and make new friends at this all inclusive space. If you can, it’s worth snapping a photo of the front of Bobby’s to capture that classic, Chicago brown brick.

2. Charlie’s Chicago

If you want to get a taste of western life in the windy city then this is the place to be. Just around the corner of Bobby Love’s is Charlie’s Chicago. A western themed bar and club that is always open late and has a ton to offer. Enjoy karaoke nights, drag shows, bingo and other thrilling events! If you’re a night owl you’ll love visiting Charlie’s Chicago.

3. Roscoe’s Tavern

Opened back in 1987 Roscoe’s is one of the most popular gay and lesbian bars in all of Halstead. Come grab some great drinks and sit in the large front area as you watch your favorite drag stars as they lip sync to your favorite songs. Then when the show has ended head on over to the dance floor where you can cut loose to the songs played by the DJ’s and may even get a chance to meet with previous stars of the show yourself. Or, just relax and enjoy a game or two of pool with some new friends. If you enjoy a welcoming space with lots to do this is the place to go to.

4. Scarlet Bar

If you’re looking for a place where you can let out your frustrations by dancing long into the night, then Scarlet is the place to go. This bar is a dimly lit, single room space that is filled to the brim with energy and is a great place to just cut loose and dance like your life depends on it. You can also try some of their delicious cocktails, including their signature Scarlet margarita. Whether you come just to hang out or enjoy one of the popular events, you’ll party all night long at Scarlet.

5. The Closet

The Closet is located just a bit off the block from the main Boystown area is a quaint little dive bar where you can meet many of the people in the local queer community. Here you don’t have to feel pressured to look hot as you yell over the loud music and trip over other people as they grind across the dance floor. Most of the bars in North Alstead cater to gay men exclusively, but here at the closet they make sure that everyone feels welcome in this space.

6. Replay Lakeview

If you love classic video games, and a rotating stock of beers then you’ll love Replay. They make sure to cater to the gay community by hiring bartenders who are actually part of the community and make sure that everyone who comes in can play games and enjoy their drinks without fear of harassment. So if you want to spend a night playing your favorite classic arcade machines while also enjoying a cold mug of your new favorite stout then Replay is a must see. Pro tip: get a photo of the fire escape stars that have been painted to look like a scene from Donkey Kong. This is a great spontaneous hang out spot, or for planned events with your friends.

7. Kit Kat Lounge

If you’re wanting to check out a bar with a flashy Hollywood feel and a rotation of incredible and beautiful drag queens then the Kit Kat lounge is the place to be. By entering this bar you’ll feel like you’re entering one of the best parties of your life and when you leave you’ll feel even more excited and fabulous than you felt before. Drinks always come with a little something extra to make them even more fabulous than before, glow sticks, glitter, candies, you name it! Then of course the food is some of the best you’ll have in the area. It’s no wonder you need to get a reservation to guarantee a spot here, with how fabulous things get here who would ever want to leave?

8. Dorothy Downstairs

While there are various locations in Chicago that welcome lesbians, Dorothy Downstairs is one of the few remaining, lesbian bars. If you’re a friend of Dorothy, then this sensual subterranean cocktail lounge made for the WLW community is one of the best Lesbian bars in the city of Chicago. Located in the West Town Neighborhood on Chicago Ave, you can sip creatively curated cocktails in this 70’s inspired lounge and simply be yourself. If you’re really lucky, you can check out some events on their calendar and enjoy variety shows held by trans individuals, drag trivia nights, girlfriend hours, and of course musical shows that are made to blow you away. This bar, filled with chic decor is a sexy tribute for queer women, made by queer women. Check it out! The folks here urge you to check out the events calendar to ensure they aren’t closed for a private engagement.

9. Whiskey Girl Tavern

If you just happen to be walking down Clark St, and love watching women’s sports, or going to a bar that is named for a beloved pooch then Whiskey Girl Tavern is the place to be! Named after the owner’s dog “Whiskey” this is lesbian owned sports bar has become a local favorite. Here at this bar on Clark St, you can enjoy some great drinks, delicious food, and watch your favorite womens sports teams play on tvs all around you. Yeah, there are various locations that serve up Chicago’s tavern style pizza, but the Whiskey Girl’s is worth trying. You can also enjoy a relaxing round of pool with your favorite girlfriends, or stay out late for those late night dance parties they have as well.

10. Nobody’s Darling

If you want to step away from the club atmosphere but still want to enjoy a relaxing night filled with class and sophistication. Then this cocktail lounge is the place for you to hit. Located on West Balmoral Ave in Andersonville, Nobody’s Darling was created for the queer community of Chicago who didn’t seem to have a classy and sophisticated place that was exclusive for them. Nobody’s darling is a notable Queer and Black owned business that encourages its patrons to embrace themselves as the outcasts they are. It serves as the perfect place for everyone to show their pride and find the community they need with each other.

If you happen to be in Andersonville, don’t forget to check out the SoFo tap. It’s a laidback queer friendly spot that’s dog friendly – perfect for day drinking before a night of partying.

Other Notable Locations to Check out

Of course visiting the neighborhood bar and sipping on creative cocktails is a great way to spend your time in the city. However, that’s not all that Chicago has to offer for the gays and lesbians who want to spend their time in the city. There are various locations and events in the area that you should consider checking out.

Gerber Hart Library and Archive

Located in Rogers Park is a place filled with LGBTQ history. Here at the Gerber Hart Library they are proud to showcase the largest circulating collection of LGBTQ books and historical items that are available to check out in the entire Midwest. Here you can learn about the history of the community, as well as learn about the various sexual orientations that are defined by queer people.

If you love learning about history and want to enjoy a quiet afternoon in a cozy space then the Gerber Hart Library and Archive is a place you should definitely put on your list. Take a look at the events calendar before you visit, there’s almost always exciting and educational programming.

Leather Archives and Museum

This adults only museum is the place to go if you are interested in the history of the leather lifestyle and want to check out an exhibition filled with kinky props and maybe even get some ideas for some fun in the bedroom. Then of course if visiting the Leather Archives and museum puts you in the mood for a leather bar experience. You can go right on over to North Halstead and visit Cellblock.

Midsommar Fest

Celebrate summer and kick off pride at the Midsommar fest. Going strong for nearly 60 years this festival offers live music on five different stages. Great food and shopping options made by local vendors, and is one of the most beloved festivals in all of Chicago. Midsommar Fest is undoubtedly one of the most exciting events of the year in the Windy City.

BackLot Bash

An annual outdoor festival that is approaching its 21st year of going strong. The back lot bash is a 2 day long music festival that welcomes talented LGBTQ stars from all around the world. Here you can enjoy great music, meet new friends, and capture many different photo ops as you spend your pride weekend enjoying the Backlot Bash.

Chicago Pride Fest and Parade

Held on the last Sunday of June, the Chicago Pride fest is one of the most significant and eye catching LGBTQ events in the entire country. This event is basically an all day party where you can eat great food, have fun, make new friends, and do so much more as you let the energy of pride wash over you.

Pride Arts Center

Pride Arts Center is a queer-friendly theater company that features several productions and other events throughout the year. It’s a great place to see an amazing show and maybe get a photo with an up and coming star.

Exploring Chicago With Taimi!

If you’re wanting to celebrate pride, or are wanting to find a place where you can unapologetically yourself. Then Chicago is one of the best cities in the country for you to check out. With one of the most prominent LGBTQ communities in the country, as well as multiple bars, lounges, and locally owned restaurants to stop in at. Taimi can also help you find other queer events, especially if you’re one who wants to remain sober during your time there. So if you’re wanting to find a place that’s queer friendly, keep this page bookmarked and be sure to download Taimi for an amazing opportunity to connect with others.

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Alan Schin

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