Top 5 ways you are guaranteed to have fun in Chicago

Photo by Joshua Mellin

Chicago is the ultimate summer city, with gorgeous beaches lining the skyline of skyscrapers, where rooftop lounges, glamorous pools, and the city’s trademark outdoor patios beckon with their breezy evenings and stunning views.

But there is more to Chicago than just lounging around being glamorous—Chicago has a seriously fun side too. For locals and visitors alike, here are our Top 5 favorite ways to have a good time in Chicago:

Bunches of drag brunches

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Chicago has several spots for a rowdy drag brunch. Hamburger Mary’s, The River Kitchen & Bar, and Kit Kat Lounge & Supper Club are three popular spots for drag brunch on Sundays. As a bonus, all three have good food too. So come to eat and stay for the show. If you can’t have fun at drag brunch, just stay home!

Showtunes at Sidetrack

“Musical Monday” nights at Sidetrack are an institution in Boystown. If you’ve never been, go and stand in the middle of the hordes of gay male theater aficionados, most of whom have had a few cocktails, and wait for the musical theater videos to come on the giant TV screens. You think this a singalong? That’s the least of it. All hell breaks loose! It is absolutely one of the most fun things to do in Chicago.

Very event(ful)

Chicago has some of the biggest summer events in the U.S.: International Mr. Leather is every May, Pride is every June, and Northalsted Market Days is coming up in August. There are festivals almost every weekend in Chicago, including the legendary music festival Lollapalooza, which lands in Chicago this August with eight performance stages, and will feature Kacey Musgraves, who won a Grammy for her pro-gay, sex-positive country song “Follow Your Arrow.” Acts also performing include Ariana Grande and Childish Gambino (photo above). It’s going to be amazing!

Get high (up)

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Chicago has numerous observation decks and rooftop lounges that give great views of the city’s world-famous architecture. The Ferris Wheel was invented in Chicago, so take a ride on the giant Centennial Wheel at Navy Pier. There are also glass-bottom decks at Willis Tower (formerly called the Sears Tower) and the John Hancock Center (which may also be renamed soon). Or skip the admission ticket price and get a drink at John Hancock’s cocktail lounge on the 95th floor.

Catch a show


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Chicago has an arts scene that rivals New York as the most innovative in the U.S. The historic theaters downtown host touring Broadway musicals, but the most innovative shows happen in the city’s world-class, award-winning, change-your-life amazing theater companies like Steppenwolf, Goodman, and Lookingglass. The About Face theatre company produces shows that focus on sexual and gender identity, in the very cool Andersonville neighborhood. Chicago is also home to some of the best dance companies in the world, including Joffrey Ballet and Hubbard Street Dance. And then there is the most prestigious comedy school in the U.S., The Second City, which has trained a who’s-who of comedians on prime time TV and shows like Saturday Night Live. We could go on and on but the list is endless. Check out Chicago and see for yourself!

Related: These sexy beach pics will make you hop the next flight to Chicago