A Legacy Walk of rainbow-color totems with plaques honoring LGBTQ rights advocates lines the main thoroughfare of this anchor to Chicago’s gay scene. 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 perennial favorite). Indulge in a raspberry truffle shake from Bobtail Ice Cream before exploring funky shops, such as Hollywood Mirror, selling off-the-wall gifts like cupcake pillows. 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.
In 1900, one in every 10 Swedish-Americans lived in Andersonville. The community (three miles north of Northalsted) retains Swedish character while being the second-largest LGBT-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 and a grocery, but it also includes vacation-worthy amenities such as a spa and locally-made meals delivered to your suite.
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.
The 40th annual Northalsted Market Days (August 6-7) 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. This year’s lineup includes Anastacia, Michael Jaé, Ginger Minj, Matteo Lane, Ada Vox, Sammy Rae and The Friends, Jaimie Wilson, Isis Muretech, and more!
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 18-19), which features live music on three outdoor stages from performers including CupcakKe, Dorian Electra, Alaska Thunderf*ck, Netta, and The Aces. 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.