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101+ Gay Things to Do in Chicago

Welcome to the ultimate Chicago gay agenda, curated by a local lesbian (yours truly) and loaded with gay things to do in Chicago.

When I moved back to Chicago as a late in life lesbian, I didn’t know where to find a queer hairstylist or how to make queer friends or… where all the lesbians hang out (?!). I created this for folks moving to Chicago and fellow late in lifers. It’s also a great resource for queer travelers visiting Chicago.

Download a free gay Chicago map below for easy navigation when you’re OUT and about.

Disclaimer: Before you comment something like “this isn’t queer,” just remember everything is queer when you are. Second disclaimer: even queer-owned and queer-friendly spots have their own issues. I included all queer-owned businesses and bars in Chicago to create a cohesive guide, please do your own research. For new LGBTQ-owned businesses in Chicago and anything I missed, please leave a comment and I will add it to the list.

This post may contain affiliate links. If you use my links, I get a small percentage without costing you a thing. Thank you for using my links and supporting my blog! xoxo

To Stay

LGBTQIA-Friendly Neighborhoods to Live in Chicago

The amazing part about Chicago is that you can find queer community in just about every neighborhood. If you’re moving here, you don’t have to live in Northalsted or Andersonville (although, I DO recommend!) to be surrounded by the queer community. Queer people and families are everywhere. That said, below are a few neighborhoods that are historically queer and have a higher gay residency/amount of queer spaces.

Northalsted (aka Boystown)

First off, let me introduce you to Chicago’s official gayborhood: Northalsted (aka Boystown). Located on the northside of Chicago, Northalsted is a colorful neighborhood with rich LGBTQ+ history and a thriving queer culture. As you walk down North Halsted Street, you’ll find queer-owned businesses, queer bars, pride flags and delicious eateries. Northalsted is famous for its annual events like the Pride Parade and Market Days that attract visitors from all over the world. While it is predominantly gay men, it’s a great place for everyone to visit and live. I live right up the street – if you see me, say hi!

Andersonville (aka Lesbianville)

Andersonville (aka Girlstown or Lesbianville) is Chicago’s unofficial lesbian neighborhood. Andersonville is a laid back, community-oriented neighborhood filled with local businesses, vintage and thrift stores, queer bars, some of the best restaurants in Chicago (IMO), and you guessed it – lesbians. Andersonville hosts many events throughout the year, such as the annual Midsommarfest, a lively street festival celebrating the neighborhood’s rich culture. Whether you’re moving here or just visiting, I highly recommend strolling down Clark Street.

Uptown

If you’re a budget gorlie moving to Chicago and are looking for a queer neighborhood, Uptown is a great option. I used to live in Uptown and found a 1-bed in a high rise for $950/month. It’s not polished or luxurious like River North or Lincoln Park, but Uptown is historic, up and coming and extremely underrated!

Uptown is close to Northalsted and Andersonville, but also has a rich history and culture of its own. The neighborhood is home to a variety of LGBTQ+-friendly establishments, including bars, clubs, and performance venues. The iconic LGBTQ+ bar, The Baton Show Lounge, has been a staple of Uptown for decades, offering drag shows and entertainment. Additionally, Uptown has a thriving arts and music scene, with renowned theaters like The Green Mill and The Riviera Theatre. It’s also home to Little Vietnam, Chicago’s Vietnamese neighborhood, where you’ll find Asian markets and Vietnamese restaurants.

A Few Others

Depending on what you like, I also recommend Roger’s Park, Logan Square, Wicker Park, West Town, Pilsen, and Edgewater. If you are looking for housing/roommates, check out LGBTQ+ Roommate Exchange on Facebook.

LGBTQ-Friendly Hotels in Chicago

If you have friends coming to visit, here are the queer-friendly hotels in Chicago I always recommend:

To find an affordable Airbnb in Chicago, click here.

Eat and Drink

Queer Bars in Chicago

Lesbian Bars

@courtneytheexplorer

Whether you’re visiting or from Chicago, Nobody’s Darling in Andersonville is the queer bar I recommend to everyone! [a d] With its recent new expansion, this James Beard recognized lesbian bar is the perfect mix of a cozy neighborhood bar and stylish cocktail lounge. They are utilizing the new expanded space to build community with events ranging from Singles Mixers, Sunday Teas to non-profit events and industry panels. Check out their website and Instagram (@nobodysdarlingbar) for events and more information. 🏳️‍🌈🏳️‍⚧️ #Andersonville #NobodysDarling #LGBTQChicago #LesbianChicago #ChicaGoandKnow #ChicagoNeighborhoodGems

♬ original sound – Courtney | LGBTQ Travel

Gay Bars

LGBTQ+ Nightclubs

  • Club Escape (gay dance club featuring house and hip-hop music)
  • Fantasy Nightclub (VIP membership gay club in Northalsted)
  • Hydrate Nightclub (gay, late-night dance club with a rotating DJ line-up)
  • Smart Bar (independent nightclub that offers varieties of dance music from cutting-edge DJs)

LGBTQ-owned Restaurants

Breakfast

Lunch/Dinner

Bakeries + Desserts

@courtneytheexplorer

After headlines of bakeries refusing LGBTQ+ couples for wedding cakes, Jenne Vailoces opened up her own bakery in 2016, Jennivee’s Bakery. Her mission was (and is) to provide visibility and employment for the LGBTQ+ and Filipino communities. Jennivee’s Bakery is best known for its delicious cakes and cupcakes. My favorites are the cookies and cream, purple red velvet, and chobeh. 10/10 ❤️‍🔥🧁🏳️‍⚧️🏳️‍🌈

♬ Oh Simple Things Where Have You Gone (Remix) – Nikolazz & Keane

Coffee Shops

Also check out Best Vegan Restaurants in Chicago and Best Vegan Desserts in Chicago.

Drag Brunch in Chicago

  • The Baton Show Lounge (long-running drag show lounge, serving brunch and bottomless mimosas on Sundays)
  • Furama (“Dim Sum & Drag”)
  • Kit Kat Lounge (iconic restaurant and lounge with nightly drag and weekend drag brunch)
  • Lark (Northalsted bar & restaurant that serves comfort food and weekend drag brunch)
  • Lips Drag Queen Show Palace (Vegas-style drag shows and fabulous weekend brunch – blogger’s choice!)

Gay Happy Hours

  • Every day – $8.95 martinis at Kit Kat Lounge (5-7pm, M-F)
  • Monday – half off bottles of wine at Lark (with purchase of entree, 5-9pm)
  • Wednesday – line dancing at Charlies (7-10pm)
  • Thursday – $4 premium well cocktails + tall boys and free darts at The Sofo Tap
  • Friday – $25 weekend buckets at Replay Lakeview

Sober Queer Spaces in Chicago

Gay Things to Do in Chicago

LGBTQ-Owned Businesses

LGBTQ+ Landmarks and Museums in Chicago

@courtneytheexplorer

Qu33r people have and always will exist. This is one of my favorite g@y things to do in Chicago. 🏳️‍⚧️🏳️‍🌈 #lgbtchicago #lgbtqchicago #northalsted #legacywalk

♬ New Abundance – Omar Enfedaque

LGBTQ+ Art Galleries

@courtneytheexplorer

ad | Founded in 2018 by Whitney LaMora, The Martin is an artist-first, full service gallery and creative space located in Chicago’s West Town. Check out their newest exhibition, Mirror Mirror which explores the theme of reflection, all physically mirrored or having a reflective element to them. It’s two rooms (technically three, make sure to explore the gallery’s bathroom which has a mini art show, The Robin). 📍 The Martin, West Town 🗓️ Mirror Mirror exhibition is open until September 30 ⏰ Saturdays and Sundays 1-4pm (staffed gallery hours), also available to see during Split Rail’s hours every day 💡 Makes for a fun queer date night; first see the art show, go for dinner at Split Rail, then go for a cocktail at Dorothy. Check out their website for queer events. Follow @courtneytheexplorer for more LGBTQ+ Chicago 🏳️‍🌈🏳️‍⚧️ #themartin #westtown #chicaGOandKnow #chicagoneighborhoodgems @themartinchicago

♬ Synchronize (Instrumental) – Milky Chance

Queer Theater + Comedy + Things to Do

@courtneytheexplorer

@thelesbianlodge aka “The funniest d*kes in Chicago” was 10/10. To live, laugh, lesbian, you can find tickets to their next show on @eventbrite. #ad #eventbritepartner #youvegotplans 📍 The Lincoln Lodge, Logan Square, Chicago 🎙️ Hosted by Emma Day. Produced by Christian Borkey and Sarah Whitcomb. ⭐️ Comedians shown: Jane Peterson, KJ Whitehead, Farai Gotora, Denae Wilkins, Courtney Tua, and Jordan Hayes

♬ original sound – Courtney | LGBTQ Travel

Annual LGBTQ+ Events

  • Market Days (weekend-long, live music street festival celebrating the LGBTQ+ community in Chicago’s Northalsted neighborhood)
  • Pride Parade (held on the last Sunday in June, Chicago’s Pride Parade is one of the largest attended Pride parades in the world)
  • Pride Fest (a two-day street festival in June, celebrating LGBTQ+ life, culture, and community)
  • Reeling LGBTQ+ Film Festival (LGBTQ+ international film festival)
  • Southside Pride (an annual street festival celebrating the life, legacy, and history of Chicago’s Black and Brown LGBTQ+ community)

LGBTQ+ Parties, Sports Clubs, and Social Gatherings

Sapphic Spaces, Parties, and Producers

Sober get-togethers

  • Lez Get Together (curates booze-free events and gatherings for the Chicago lesbian community)
  • Queer Sober Social (hosts virtual and in-person events in Chicago for sober or sober-curious member of the LGBTQIA+ community)

Local’s Gay Guide to Chicago

Bath house

Gym

Queer Hair Salon’s and Barber Shops

  • Alex Oh My (cool cuts + color, neurodivergent-friendly, use code “a friend of Courtney” for $20 off any service)
  • Barbara&Barbara (queer owned-and-operated, LGBTQ+ centric hair salon)
  • Chicago Male Salon (inclusive salon in Boystown, offering a full range of hair styling  and skincare services)
  • Fern and Moody Salon (Queer owners Francesca and Jackie help fellow queer folks get the hair they want, in a cool and inclusive atmosphere)
  • Handsome Bastard Barber Shop (specializing in “effortless style”, from classic to modern cuts)
  • Salon Glow Chicago (modern, chic salon specializing in blonding and hair extensions)
  • Twisted Scissors (edgy, unique styles and vibrant colors)

Queer-Owned Med Spa

Nail Salon

Home Services

Legal Assistance

  • Lambda Legal (a dedicated legal team and civil rights organization that focuses on the LGBTQ+ community )
  • Metz + Jones (Chicago-based LGBTQ+ probate, real estate, and estate planning  law firm)
  • Transformative Justice Law Project of Illinois (a collective of lawyers, social workers, and activists who provide free legal services to low-income trans and gender non-confirming persons)

LGBTQ-Friendly Medical

Queer Photographer

Queer Therapists

Queer Resource Centers

Queer Sports Leagues, Clubs, and Activities

For sports lovers who prefer watching, I recommend watching games at Whiskey Girl Tavern, a lesbian-owned sports bar in Edgewater. There are multiple Pride-themed Chicago sports games all year-round including Cubs Pride Night, Sox Pride Night, Blackhawks Pride Game, Red Stars Pride Game, and more.

You could also support Chicago queers (aka women’s sports) by going to a Chicago Sky, Red Stars, or Women’s Rugby game!

Where to Find Events, Things to Do, and Queer Friends in Chicago

Top 25 Gay Things to Do in Chicago

  1. Touch the Bean (aka Cloud Gate)
  2. Go Thrifting + Vintage Shopping in Wicker Park
  3. Queer Theater at PrideArts
  4. Go to the queer comedy show Baby Wine at the Annoyance Theater
  5. Stroll around Garfield Park Conservatory
  6. Eat the rainbow at The Original Rainbow Cone
  7. Have a drink at Chicago’s lesbian bar, Dorothy
  8. Go to a queer event at Eli Tea Bar
  9. See a broadway show downtown
  10. Check out Sidetrack’s monthly story-telling event, Outspoken
  11. Go to Gerber/Hart Library, Chicago’s gay library
  12. Do the self-guided Legacy Walk tour
  13. Go to the Leather Archives and Museum
  14. Celebrate Pride at Chicago’s Pride Parade
  15. Head to LGBTQ+ street festival, Market Days
  16. Stop by Unabridged Bookstore
  17. Go for drag brunch at Lips Drag Queen Show Palace
  18. Go to date night at Wood
  19. Do a beach day at Hollywood Beach
  20. Picnic at AIDS Garden Chicago
  21. Get breakfast at Tweet
  22. Take photos with the rainbow crosswalks in Northalsted
  23. Shop til’ you drop at local shops in Andersonville
  24. Get cocktails and sit on the patio at Nobody’s Darling
  25. Go to a queer party or concert at Sleeping Village

What’s your favorite gay thing to do in Chicago? Did I miss anything? Comment below!

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