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 Boystown) 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.
LGBTQ friendly establishments abound throughout the city. For cheese-and wine-lovers, Pastoral carefully curates its artisan cheese plates, wine lists and gift sets at six Chicagoland locations, including in the Loop near the shops at Block 37. At P.O.S.H., 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.
Unique arts and crafts, along with State Fair-esque foods such as deep-fried Twinkies and Champagne-lemonade slushes, fill Boystown during the largest outdoor street festival in the Midwest (August 12–13 this year). More than 180,000 visitors come to check out music on five stages (past headliners included Salt-N-Pepa and Olivia Newton-John) and more than 400 vendors that line North Halsted Street.
Honoring freedom of expression since the aftermath of the police raid on New York City’s Stonewall Inn gay club in 1969, Chicago Pride draws nearly a million revelers over its two-weekend span. The first weekend (June 17–18 in 2017) features pulsing music on outdoor stages and inside hopping bars along the North Halsted strip in Boystown (part of the East Lakeview neighborhood). The following weekend, crowds pack the same area, waving rainbow flags as creatively costumed revelers and more than 250 floats take part in the Pride Parade.
The Great River Road, which travels along the Mississippi River, has countless o...