Pride of Chicago

Home to the first officially recognized gay village in the United States and one of the world’s most celebrated pride festivals, the Windy City embraces its LGBTQIA+ community.

in Arts & Culture, Chicago
May 10, 2023

Photo Adam Alexander, Courtesy of IOT.

Chicago is a famously LGBT friendly destination.

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Hot Hangouts

Northalsted

The Legacy Walk is the world’s only outdoor LGBTQIA+ History Museum Walk, consisting of rainbow-color totems with plaques honoring queer rights advocates along Chicago’s North Halsted Street Corridor, between Belmont Avenue and Grace Street in the Lakeview neighborhood.

It’s also known for drawing foodies with unique establishments, such as the Chicago Diner, which has been serving vegetarian comfort food since 1983 (the Cajun black bean burger is a local favorite). Indulge in a cannabis-infused (or not) blueberry hibiscus lemonade or pistachio latte from Wake-N-Bakery before exploring kitschy shops such as Belmont Army Vintage, which sells vintage finds - perfect for a night out. Belt out show tunes on Mondays, Fridays and Sundays at Sidetrack bar or dance to pop music and catch a drag show at Roscoe’s. Cap it all off with killer oversized cocktails at D.S. Tequila Company.

Andersonville

In 1900, one in every 10 Swedish Americans lived in Andersonville. The community (three miles north of Northalsted) retains its Swedish character while being the second-largest LGBTQIA-populated neighborhood in the city.

The Swedish American Museum tells the story of the community’s move to the city’s North Side after the Great Chicago Fire of 1871. Svea Restaurant dishes up saucy Swedish meatballs and crepe-like Swedish pancakes. Whether you’re staying for one night or a week, the 25-suite Guesthouse Hotel feels like home with full kitchens, but it also includes vacation-worthy amenities such as a spa and locally-made meals delivered to your suite.

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A group of men take a selfie in the famous Sidetrack gay bar in Boystown, Chicago. Photo, Adam Alexander, courtesy IOT.

Around Town

You’ll find friendly establishments abound throughout the city. Wine lovers will rejoice at Pops for Champagne, with over 100 bottles of champagne, sparkling wines, bar service, raw bar, and dessert menu. At P.O.S.H.—just 100 feet away— discover rare flea market finds from France and England—plus trendy dinnerware sets and vintage jewelry—in a beautifully preserved Queen Anne-style building in River North.

While hidden to passersby, downtown’s Second Story Bar (above Sayat Nova restaurant off North Michigan Avenue) is worth seeking out for its delightfully divey feel (complete with a worn red carpet) and diverse clientele.

Northalsted Market Days

The 41st annual Northalsted Market Days (August 12-13) a weekend-long live music street festival celebrating the LGBTQ community in Chicago’s Lakeview neighborhood. This 1/2-mile-long festival features all-day lineups of performances on six stages, 250+ unique vendors, arts, crafts, food and drink, DJ’s, dancing, and sponsor booths. Last year’s lineup included Anastacia, Michael Jaé, Ginger Minj, Matteo Lane, Ada Vox, Sammy Rae and The Friends, Jaimie Wilson, and Isis Muretech. Stay tuned for this year's line-up - coming this spring!

One Colorful Party

Honoring freedom of expression since the aftermath of the police raid on New York City’s Stonewall Inn in 1969, Chicago Pride draws nearly a million attendees over its two-weekend span.

The first weekend’s highlight is Chicago Pride Fest(June 17-18), which features live music on three outdoor stages from performers including Heather Small, Slayyyter, Jordy, Eureka O'Hara and many more. The following weekend, crowds pack the same area to catch a view of more than 250 floats taking part in the city’s annual Pride Parade.