Midwestern guys are wholesome, friendly and fun to have around. They’re rugged and have an adorable accent. There is something about Midwestern guys we just can’t resist. So let’s take a trip to the biggest city in the Midwest — Chicago, of course.
Chicago is a beautiful city with a thriving art and music scene. For architecture fans, the Windy City has sleek designs. Chicago is also home to some of the tallest buildings in the world, like the John Hancock Center or the Willis Tower (formerly known as the Sears Tower).
Chicago also has a rich gay history. Old Town was the first gay district in Chicago, starting around 1920. In 1961, Illinois became the first state to decriminalize consensual sodomy. In 2006, Chicago was the host of the Gay Games. Illinois also started recognizing civil unions in 2011 — and legalized marriage equality in 2014, a year before the rest of the country!
Given its history, no wonder Chicago’s known as a top gay destination. Besides visiting Boystown for drinks and socializing with locals — that’s obvious — here are some of our favorite places to check out in Chicago.
Unusual Chicago Attractions
If you love to learn about history, you’ll want to make some time for the Pullman National Monument. The first model industrial town in the nation, this charming neighborhood is still an active community. As you take a leisurely walk around the area, you also learn the history behind the buildings.
Chicago also has excellent markets for avid shoppers. The Randolph Street Market, one of the few year-round markets, is the best place to find antiques in Chicago. The Randolph Street Market also hosts live entertainment during the weekend and holidays to keep you amused while uncovering your hidden treasure.
At the Logan Square Farmers Market you can buy organic products and hard to find spices here. Logan Square also has free live entertainment every Sunday. The lively atmosphere means shopping here is always an adventure — but in a good way.
The 606, open since 2015, is a trail connecting Logan Square, Humboldt Park, Wicker Park and Bucktown. This trail is easily the most scenic way to see the northside of Chicago. Locals and visitors alike can bike, jog and walk along this 2.7 mile path.
Unique Chicago Museums
There are more than 30 museums in Chicago for culture vultures. There is the Museum of Modern Art for the contemporary art fans. The Museum of Science and Industry is a must-visit place for tech hounds. However, if you prefer a unique experience, there are several one-of-a-kind museums you should check out.
McCormick Bridgehouse & Chicago River Museum is one of the only museums in the world devoted to bridges. The McCormick Bridgehouse demonstrates the dynamic relationship between Chicago and its river as well as other famous moveable bridges around the world. Visitors get to go behind the scenes and see how different moving parts work together to lift the large Michigan Avenue bridge leaf.
For you Folsom fans, you’ll have to go to Chicago’s Leather Archives & Museum. The LA&M is devoted to the history of the leather, kink and fetish lifestyles. (They’re also home to International Mr. Leather.) Not only do they have a huge collection of leather and fetish gear, it also provides an educational experience for a mature audience. The LA&M opens its collection to experts and researchers as well as anyone interested in the history and culture of leather.
Chicago prides itself on its diversity. Chicagoans can learn about different cultures from centers like the Chinese-American Museum and National Museum of Mexican Art. The Chinese-American Museum shares stories about Chinese immigrants in the Midwest. This museum showcases Chinese heritage featuring traditional garments, artifacts from local Chinatown associations and special events like the Mid-Autumn Festival celebrating Chinese culture.
The National Museum of Mexican Art has over 10,000 pieces in its permanent collection. With an art collection that big, it’s easy to immerse yourself in the amazing world of Mexican art. The collection spans both sides of the border, featuring work from Mexican-American artists as well. It hosts special events throughout the year, like Dia de los Muertos After Dark. And the best part? It’s free to get in.
Gay Chicago Nightlife
Midwest boys love a good time. From socializing at a cozy bar to dancing the night away at a massive club, gay Chicago is never short on fun.
If you want a little slice of the Berlin nightlife in Chicago, this bar is just as good as flying there. Berlin hosts drag shows and music theme nights — including tributes to legendary Chicago record label Wax Trax! No wonder so many Chicagoans call it the best nightclub in town!
Thirsty? Make sure to Hydrate! This nightclub has attractive men, fun drag queens and hot strippers. Hydrate also hosts daily events from RuPaul’s Drag Race viewing parties to K-pop nights. Hydrate always draws a fun crowd.
With a name like Big Chicks, who can blame us for being intrigued? And they reward our interest with a massive cocktail menu and delicious burgers and quesadillas. Big Chicks also has an art gallery featuring women in provocative poses. The unique exhibit started about 30 years ago and features local unknowns alongside internationally known artists. Be sure to check out the art when you’re here!
Roscoe’s Tavern is another great spot in gay Chicago to catch a live performance or just socialize. This place hosts marquee entertainers regularly. If you are a big RuPaul’s Drag Race fan, Roscoe’s Tavern has queens of all seasons sashay the stage for their adoring fans.
If you want to keep it cozy, Charlie’s is a down-home country bar with friendly staff, cheap drinks and sexy cowboys. At this attitude-free bar, you can sing along with drag performers or dance around the room in your leather chaps.
After all that partying, are you ready to relax? Steamworks is a gym with saunas, a public play area, private rooms and more for discreet encounters. In addition to state-of-the-art equipment, this multi-level facility has a fireplace lounge for guys to hang out, plus open and private spaces for cruising.
Gay Chicago Events
It’s not just about the gay bar scene — gay Chicago is home to a number of events. If you happen to find yourself in Chicago in August, you must check out the Northalsted Market Days. The two-day event has a variety of vendors, arts, food and entertainment. This big outdoor street festival always features famous entertainers like Big Freedia, Tiffany, Jody Watley and other local artists partying alongside festival goers.
As we alluded to above, the International Mr. Leather Weekend is a huge deal. This yearly celebration brings the leather, kink and fetish community together, usually in May. The International Mr. Leather Competition is the main event, but there are also loads of vendors as well as educational workshops for the community. The whole thing ends with the infamous Black and Blue Ball — where anything and everything goes.
Feature image by LeoPatrizi via iStockphoto.com