The first weekend (June 17–18 in 2017) features pulsing music on outdoor stages and inside hopping bars along the North Halsted strip (part of the East Lakeview neighborhood). 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. 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. Unique arts and crafts, along with State Fair-esque foods such as deep-fried Twinkies and Champagne-lemonade slushes, fill Northalsted during the largest outdoor street festival in the Midwest (August 12–13 this year). 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. 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.
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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. LGBTQ friendly establishments abound throughout the city.
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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. Svea Restaurant dishes up saucy Swedish meatballs and crepe-like Swedish pancakes. 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. The community (three miles north of Northalsted) retains Swedish character while being the second-largest LGBT-populated neighborhood in the city. In 1900, one in every 10 Swedish-Americans lived in Andersonville. 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.
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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. 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). 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.