Gay Summer Getaway: Chicago

Summer in Chicago is packed with can’t-miss events that celebrate music, culture, and the city’s LGBTQ+ pride. Pride Month festivities include Chicago Pride Fest (June 21–22), a lively two-day celebration in Northalsted featuring performances by Natasha Bedingfield, JoJo Siwa, and Bob the Drag Queen; the Chicago Pride Parade (June 29), one of the city's most beloved traditions, drawing thousands of people to the streets in a powerful display of unity and inclusion; and Pride South Side (July 5), a joyful day of performances and community hosted by The DuSable Black History Museum.

Two groundbreaking art exhibitions also make Chicago a destination for cultural exploration this summer. Opening July 5, the Museum of Contemporary Art Chicago presents City in a Garden: Queer Art and Activism in Chicago, a powerful intergenerational exhibition spotlighting the city's often overlooked contributions to LGBTQ+ art and activism.

Meanwhile, Wrightwood 659 is hosting The First Homosexuals: The Birth of a New Identity, 1869-1939 (through July 26). This unprecedented exhibition, with more than 300 works by more than 125 artists from 40 countries, is on loan from over 100 museums and private collections across the world, including the Musée d’Orsay, The Tate, The Courtauld, The Metropolitan Museum of Art, Kunsthaus Zürich, and National Museum of Denmark, with a number of national treasures which have never before been allowed to travel outside their countries. 

Music lovers can experience a wide range of performances throughout the summer, from house to jazz to global pop superstars. Lollapalooza (July 31–August 3), one of Chicago’s most highly anticipated summer events, features a line-up packed with the music industry’s biggest names, like Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, Rüfüs du Sol, Luke Combs, A$AP Rocky, Gracie Abrams, and Doechii, along with local favorites and emerging artists. Chicago House Music Festival and Conference (August 22–23) and the Chicago Jazz Festival (August 28–31) will fill Millennium Park with free concerts that celebrate the city’s deep musical roots.

End the summer with two of the city’s most beloved traditions: Chicago Air and Water Show (August 16–17), featuring breathtaking aerial stunts over Lake Michigan, and Taste of Chicago (September 5–7), a massive culinary celebration in Grant Park showcasing the best of the city’s food scene. Whether you’re drawn to world-class art, electrifying music, or delicious food, there’s something for everyone in Chicago this summer.