Gay Local Tips in Chicago

Visiting Chicago, America's windy city

Rito and Garrett are a couple of hosts from Chicago. They were excited to share their tips on how to take advantage of this great American city. They told us about the best bars, the coolest locations and their secret spots so that you can take advantage of this iconic city in an authentic way. Don't forget to indulge with a delicious Chicago-style pizza, get a citybike and ride along the incomparable waterfront, and maybe check out a Chicago Cub's game. Explore Chicago. Experience your pride.

How gay-friendly is your city? What’s gay life like there?

Our city is extremely gay-friendly! You see happy LGBTQ couples everywhere you go, and Chicagoans are generally very welcoming and open-minded. There’s Boystown, which offers nearly half a mile of shops, gay-owned businesses, restaurants, clubs, and bars. Then there are several gay destinations off the beaten path, ready for you to explore. All year long there are street festivals, parades, and other events ranging from mild to wild!

What are the best gay events that take place in your city each year?

Pride is a huge event here, offering one of the largest parade routes in the USA. It is a blast for everyone, from kids to adults. Market Days is the largest gay street festival in America, and takes over Boystown, with three nights of live performers, drag shows and more. For our kinky friends, there’s International Male Leather, which occupies the Congress Hotel downtown, and features a wide variety of panels, discussions and of course, parties.

We only have 48 hours in your city. What can’t we miss?

A visit to one of the many rooftop bars to enjoy a bird's-eye view of the city, a trip to one of the delicious restaurants in West Loop (Au Cheval has, like, the best burgers in the world), a miniature bar crawl in Boystown (to enjoy the eye-candy and to see an iconic section of America’s LGBTQ history), and if you’re into art you can check out some of the contemporary galleries on Chicago Avenue or the Art Institute of Chicago which is absolutely humongous.

What’s your favorite gay place to grab a bite for lunch? A nice dinner?

Well for lunch we recommend Beatnik on the River, which offers bohemian-inspired decor, Chicago River views, and of course amazing cocktails and food. For dinner, try booking a table at Wood in Boystown, the name is a cheeky ode to the area, and the food is modern American fare along with classed-up cocktails that also utilize sexual innuendo (and high-end ingredients).

A gay place for brunch on weekends?

Kit Kat Lounge in Boystown no doubt, but reserve your table in advance. It takes drag brunch to another level. Talented performers, delicious food, and undoubtedly lots of Bloody Mary’s and Mimosas make this an enjoyable experience.

Best gay place and day for a cheap beer or happy hour?

Progress Bar has power hours on Friday with vodka specials, plus their lighting installation is super cool. Roscoe’s offers a rotating pitcher of mixed drinks every weekend for $30. Also, there’s always Town Hall Pub in Boystown, where you can purchase trays of Jell-O shots for like $10!

We’re ready to party! What are the best gay clubs?

If you’re here on a Sunday and have a taste for house music (Chicago is the HOME of house music) then there’s no better event than Queen at Smart Bar. You may find legendary DJs like Derrick Carter playing, famous drag queens like Lucy Stoole hosting, and a safe environment no matter where you fall under the gay spectrum. Berlin is also great for 80s dance nights, Roscoe’s for Britney Spears’ nights and Splash has an excellent illuminated dancefloor and even better music.

What are the best alternative gay bars and clubs where you live?

If you’re not afraid of a bit of exploration, the Jackhammer Complex has a lot to see. From your normal gay bar up top that hosts drag shows, to The Hole, a basement bar downstairs with all sorts of wild features and areas, if you catch our drift. You can also enter The Hole through the sex shop next door, which features some of the most unique gear available in the city.

Are there any places related to LGBT history?

The Leather Archives Museum in Chicago offers a unique perspective of the fetish genre throughout time, plus the owner of the museum was the owner of one of the original bathhouses in the country, adding further intrigue. Boystown is more than bars too, there's the Legacy Walk, which features bronze memorial markers you can read, offering a history lesson of sorts.

Can you share a secret or little-known place to visit in your city?

Daisies, an Italian restaurant. It's our favorite place for pasta in the city. It’s in the hip neighborhood of Logan Square, and all of the pasta is made in house.

Any beaches, parks or best other places to chill out?

In the summer you can’t miss a day trip to Kathy Osterman Beach, aka Hollywood Beach. It has a beach that’s predominantly gay, and even the lighthouse is decked out in the rainbow flag - an iconic spot for photos.

Where can we get the best view of Chicago?

An insider's secret is to have a drink at the “top of the cock”, at the John Hancock tower. By purchasing a drink at the Sky Bar, you get the chance to see unbeatable panoramic views of Chicago's downtown and Lake Michigan. Or you can splurge and purchase a ticket to the observation deck.

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Thinking of visiting Chicago? Check out our Travel Guide and Accommodations for this great gay city!

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