Its citizens claim Midwest is best—and Chicago lives up to the hype with a cosmopolitan arts and culture scene and LGBTQ+ footprint to match.

Kick it off in two key neighborhoods: East Lakeview (better known as Boystown and a traditional gay hotspot) and Andersonville (which lesbians historically made their own). These neighborhoods used to have a sharp divide, but today everyone’s welcome in either. (Although we will say if you’re looking for a good old fashioned gay dance party, Boystown is the better bet.)

By day, make your way to Wrigley Field, home of the Cubs. Tickets aren’t cheap, but if you love America’s pastime, they’re worth it. Or, for ballers of a different persuasion, Magnificent Mile of Michigan Avenue beckons with nearly 500 shops to spend those bills.

There’s more to Chicago than winter chill. Come in the warmer weather to be rewarded with beach time on the beautiful waterfront of Kathy Osterman Beach (make sure to check out the gay part of the beach - Hollywood Beach off Hollywood Avenue). Plus, your pick of special events like the fetish-oriented International Mr. Leather event in May or famously fabulous Market Days in August.

No matter when you breeze through, we have a feeling the Windy City will welcome you with open arms.

YOUR FILTERS     Asexual

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A lesbian, gay, queer, and transgender crowd at a gay club dancing the night way after finding the club on Rainbow Index