Skip to main content

Home Life Life Travel

Chicago’s gaybourhoods are brought to life with theatre, comedy and a warm welcome


By Steve Brown

Chicago, Illinois, is the big city where you can expect a warm Midwestern welcome.

Cradling Lake Michigan with 26 miles of publicly owned beaches, the charming metropolis has a shoreline bustling with joggers, cyclists and people playing beach volleyball in the summer.

If you’re looking to soak up some sunshine, head to gay hotspot “Hollywood Beach”, officially named Kathy Osterman Beach, in honour of a Chicago politician who fought for LGBTQ rights in the 1980s.

Throughout 2019, the city is baring its soul for the Year of Chicago Theatre, a city-wide celebration featuring productions of West Side Story and Little Shop of Horrors as well as exhibitions including one on the hit musical, Chicago

And you can take in all that jazz at The Green Mill club, or visit The Second City comedy club where Joan Rivers, Tina Fey and Amy Poehler launched their careers.

The city boasts 22 Michelin-starred restaurants, but the cheap eats serve up tasty food, too: try deep-dish pizza, Chicago-style hot dogs piled high with toppings, and caramel and cheese popcorn at Garrett Popcorn Shop. The city boasts great gaybourhoods. 

Andersonville is home to a host of shops and restaurants along Clark Street. Possibly better known is Boystown — one of the biggest LGBTQ neighbourhoods in America — and home to the two-weekend Pride festival over two weeks.

The event normally attracts about a million revellers, but there could well be more this year as the city celebrates Chicago Pride’s 50th anniversary.

Two other LGBTQ events hosted in Boystown are Northalsted Market Days, the largest street festival in the Midwest, held in August, and the Reeling Film Festival, in September. Chicago really does welcome everyone.