LGBTQ+ Businesses Olin Loves | Chicago
Chicago's LGBTQ+ Business GuideCall Olin: 312.771.1328

Chicago's LGBTQ+ Businesses Olin Loves.

These are not ads. These are places Olin actually goes, loves, and wants you to know about.

🏳️‍🌈 Real Picks. Real Community. Real Chicago.
Olin Eargle

Why This List Exists.

Chicago has one of the most vibrant, welcoming, and fiercely proud LGBTQ+ communities in the country — and the businesses that serve that community deserve to be celebrated. This isn't a sponsored directory. It's a personal list of places I genuinely love, return to, and recommend to every client, friend, and newcomer I meet.

Whether you're brand new to the city or a lifelong Chicagoan looking for something new, I hope this list helps you feel at home.

— Olin

Paper & Pencil
🛍️Andersonville
Paper & Pencil
🛍️ Stationery Shop
Queer-owned independent stationery shop in the heart of Andersonville. In-person only — and worth every visit.
💬 Olin's Take:
"Southerners moved up to Chicago too!! This little shop is a gem — great selection and so much charm. Go in, browse, buy something beautiful."
WebsiteInstagram
Defloured Bakery
🧁Andersonville
Defloured Bakery
🧁 Bakery
100% gluten-free bakery with incredible pastries, cakes, and treats. All the flavor, none of the gluten.
💬 Olin's Take:
"An awesome bakery with gluten free options — and honestly? You would never know. Everything is delicious."
WebsiteInstagram
Lady Gregory's
🍺Andersonville
Lady Gregory's
🍺 Irish Gastro Pub
An Irish gastro pub with incredible food, amazing atmosphere, and a whiskey menu that'll make you stay all night.
💬 Olin's Take:
"One of my favorite pubs — amazing food and atmosphere. And fun fact: one of my previous clients wrote the whiskey menu for them. Yes, really!"
WebsiteInstagram
Early to Bed
🏳️‍🌈Andersonville
Early to Bed
🏳️‍🌈 Queer Shop
A queer, feminist sex-positive shop where every question is welcome and every person is respected.
💬 Olin's Take:
"A queer sex shop where no question goes unanswered. The staff is knowledgeable, kind, and completely judgment-free. This is what inclusive retail looks like."
WebsiteInstagram
The Understudy
☕Andersonville
The Understudy
☕ Cafe & Bookshop
A theatre-inspired cafe and bookshop owned by two partners who traded the stage for coffee — and we are so glad they did.
💬 Olin's Take:
"Two partners own this who are theatre folks turned cafe owners — so cute! It feels like stepping into someone's beautifully curated living room."
WebsiteInstagram
Meeting House Tavern
🎯Andersonville
Meeting House Tavern
🎯 Bar & Games
A queer-friendly bar with pool, skeeball, darts, shuffleboard, and drag. Yes, all of that in one place.
💬 Olin's Take:
"One of our favorite bars — pool, skeeball, darts, shuffleboard AND drag. It is genuinely impossible to have a bad time here."
WebsiteInstagram
Rattleback Records
🎵Andersonville
Rattleback Records
🎵 Record Store
A retro record store in Andersonville owned by a true music lover. Vinyl, community, and good vibes.
💬 Olin's Take:
"My friend is the owner — and this retro record store is exactly what Chicago needs more of. Go dig through the crates. You will find something you love."
WebsiteInstagram
The North End
🏈Boystown
The North End
🏈 Gay Sports Bar
Chicago's favorite gay sports bar — the perfect place to catch a game and be completely yourself.
💬 Olin's Take:
"Our favorite gay sports bar and an awesome place to hang after a Cubs game. The energy in here on game day is electric."
WebsiteInstagram
Roscoe's Tavern
🏳️‍🌈Boystown
Roscoe's Tavern
🏳️‍🌈 Iconic Bar
One of the most iconic LGBTQ+ bars in the country. Boystown wouldn't be Boystown without it.
💬 Olin's Take:
"One of the most famous. If you are new to Chicago and you have not been to Roscoe's, that is your first assignment."
WebsiteInstagram
Kit Kat Club
🎭Boystown
Kit Kat Club
🎭 Entertainment & Dining
A legendary supper club and cabaret experience with jaw-dropping entertainment and great drinks.
💬 Olin's Take:
"Amazing entertainment and drinks. This place is pure Chicago magic — dinner, a show, and memories you will not forget."
WebsiteInstagram
Hamburger Mary's
🍔Edgewater
Hamburger Mary's
🍔 Restaurant & Bar
The legendary drag-friendly burger joint where you can Eat, Drink and Be Mary. Owned by Olin's best friends.
💬 Olin's Take:
"My best friends are the owners of this chain — and this hamburger joint lets you Eat, Drink and Be Mary!! It is loud, joyful, and absolutely fabulous."
WebsiteInstagram
Edgewater Candles
🕯️Edgewater
Edgewater Candles
🕯️ Candle Shop
A queer-owned candle company making beautiful, thoughtful scents perfect for gifts or your new home.
💬 Olin's Take:
"Awesome queer owned candle shop — great for gifts. Honestly, every new homeowner I work with gets pointed here immediately."
WebsiteInstagram
Level Sporting Club
🏅Wrigleyville
Level Sporting Club
🏅 Sports Bar
A brand new female-owned sports bar in Wrigleyville dedicated to women's sports. Game-changer — literally.
💬 Olin's Take:
"Brand new female owned sports bar — and Chicago needed this SO badly. Go support it, go watch a game, go celebrate women in sports."
WebsiteInstagram
Fred's Auto Shop
🚗Wrigleyville
Fred's Auto Shop
🚗 Auto Repair
Queer-owned auto body shop in Wrigleyville. Real expertise, real community values.
💬 Olin's Take:
"Queer owned car body shop — and you should absolutely be taking your car here. Support community, get great service. Win-win."
WebsiteFind on Facebook
Nobody's Darling
🍷Bowmanville
Nobody's Darling
🍷 Wine Bar
An off-the-beaten-path queer bar and wine spot that became a James Beard Award finalist in under a year.
💬 Olin's Take:
"One of my favorite off the beaten path wine bars. If you feel like you might have taken a wrong turn to get there — good. You found it."
WebsiteInstagram
Two Hearted Queen
☕Lakeview
Two Hearted Queen
☕ Coffee Shop
A somewhat secret queer-owned coffee shop with a totally laid-back feel. The kind of place you find and never tell anyone about.
💬 Olin's Take:
"Somewhat secret queer owned coffee shop with a laid back feel. It has the energy of your cool friend's apartment — except they serve really good coffee."
WebsiteInstagram
Bukiety Floral
🌸Fulton Market
Bukiety Floral
🌸 Floral Design
A queer-owned floral design studio doing breathtaking work for weddings, events, and everyday beauty.
💬 Olin's Take:
"Queer owned flower design company — amazing work! Whether it is a wedding or just because, the arrangements are absolutely stunning."
WebsiteInstagram
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New to Chicago? Let Olin Show You Around.

If you are relocating, exploring, or just trying to figure out where you belong in this city — Olin gets it. He was new here once too. He will personally pick you up, show you the neighborhoods, introduce you to the community, and help you find your place. No pressure. No agenda. Just real talk and good company.

Call Olin: 312.771.1328Send a Message
Olin and AndrewOlin & Andrew — Chicago locals, living it out loud.
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