The Must-Visit Gay Mecca of the Midwest

The must-visit gay mecca of the Midwest

Looking for the perfect American getaway, where boys and girls and everything in between are welcomed with open arms? Look no further than the jewel of the Midwest: Chicago.

With its stunning lakefront, world-class architecture, and vibrant cultural scene, the Windy City offers LGBTQ+ travelers an unforgettable urban experience without the international airfare. Winter can be a bitch, but Summer brings endless festivals, outdoor dining, and the perfect weather to explore this perfect mix of big-city excitement and midwestern charm.

The Gay Scene 🏳️‍🌈: Chicago's LGBTQ+ community centers around Northalsted (formerly known as Boystown), the nation's first officially recognized gay village. This historic neighborhood is packed with queer-owned businesses, bars, and nightclubs. Sidetrack's famous showtune nights and Roscoe's dance floor keep the party going year-round, while Steamworks Chicago is one of America’s last legendary gay bathhouses.

The neighborhood truly explodes during Market Days in August, the Midwest's largest street festival attracting over 300,000 visitors for two days of live music, food, and shopping across six city blocks. If you time your visit right, Chicago Pride (late June) transforms the entire city into a celebration with events spanning the entire month.

Things to See and Do 😎:

• Visit Hollywood Beach - The unofficial gay beach with beautiful Lake Michigan views

• Catch a drag show at Lips Chicago - Featuring some of the city's most talented performers

• Cruise the Chicago River - Further down from old Boystown is “downtown” Chicago—the Loop—and the river runs right through it

• Browse Unabridged Bookstore - A beloved LGBTQ+ bookshop celebrating 40+ years in the community

• Explore the Legacy Walk - An outdoor LGBTQ+ history museum along the rainbow pylons of Halsted Street

• Take in a Cubs game at Wrigley Field - The historic ballpark is just steps from Northalsted and offers a quintessential Chicago experience (with plenty of eye candy in the stands)

• Try some of that famous Chicago deep… dish - Pequod’s Pizza is one of the famous institutions that attract people from all over

• Visit the Art Institute of Chicago - World-class museum featuring works from numerous LGBTQ+ artists

• Snap a selfie at "The Bean" - The iconic Cloud Gate sculpture in Millennium Park

Where to stay: For accommodations directly in the heart of the action, Hotel Zachary ($220-280/night) offers stylish rooms across from Wrigley Field and walking distance to Northalsted's gay bars. The more budget-friendly City Suites Hotel ($140-180/night) puts you in the middle of the gayborhood. For luxury seekers, The Gwen ($300-350/night) in downtown Chicago combines art deco glamour with a rooftop bar offering spectacular city views, just a quick train ride from the gay district.

How to get there: Chicago is exceptionally well-connected, with O'Hare and Midway airports offering hundreds of daily flights. From New York, expect to pay $200-300 for a direct flight (2 hours), while Los Angeles travelers should budget $250-400 for direct flights (4 hours).

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Q&A Time:

Last week we asked if you knew the meaning behind “the gayest tattoo ever” — here are the results:

• “The fantasy of seeing some dude with this it is such a turn on - but not enough to ever try it“ GIRL SAME

• “This is the first I've heard of it! Do I have to surrender my gay card?” KEEP IT!

• “That's why I never would take one” 🫢

This week’s poll: Would you rather see more of your own country — or get out and travel the world? Tell us why in the comments!

Some *~Interesting~* Reads

News you may have missed on traveling, queers, and traveling queers 🗞️

• “HANDS OFF OUR DRAG”: last night, drag artists organized outside the Kennedy Center in D.C. to protest Trump’s attacks

• This European country just issued a travel warning to the U.S. — over treatment of trans and nonbinary people

• The United States has withdrawn from the United Nations LGBTI Core Group, dedicated to advocating for LGBTQ+ rights worldwide

• “The lynch mob mentality in this country is at an all-time high” — Madonna has once again come out swinging for the LGBTQ+ community

• Meanwhile, one state has proposed a new bill that would make being trans a FELONY

• The founder of Misterb&b claims Meta removed its ads: “It feels like censorship”

• This story is crazy: this jacked Gay MAGA travel influencer just died… while awaiting his own murder trial… after a series of other twists

• Sniffies finally released their long-awaited app — and I tried it out to see if it’s worth the fuss

• Traveling with sex toys: A safe and discreet guide for LGBTQ+ travelers

• First class tix, top-shelf liquor, $3,500 kitchenware & more: gays share their favorite indulgences

• Luigi Mangione's rumored 20 sex tapes have the internet going feral

• Train travel’s glamorous comeback — and the gays making it happen

• Nice, France hosts a queer carnival every year and you have to see it

• Travel + Leisure has put out their top 12 LGBTQ+-friendly resorts in the U.S. and Caribbean for a fun and inclusive getaway

• This low-cost airline just launched a $374-flight to Thailand — go live out your 'White Lotus' dreams (but leave your brother at home 😳)

• This airline just upgraded its unlimited “all you can fly” pass — and its shockingly affordable

• And here are 6 spring break destinations where you can still find cheap flights 👀