1. Humboldt Park’s Sizzling Fiesta 

The weekend is the Puerto Rican Fest in Humboldt Park. The festivities include the 46th Annual Puerto Rican Day People’s Parade along Division Street, leading into the festival and carnival within the park grounds. Attendees can enjoy traditional food, cultural performances, art, and more. The festival promises a colorful and immersive experience that captures the essence of Puerto Rican heritage. June 6-9. puertoricanfest.com

2. Sizzle, Groove, Art, Fest

Midsommarfest, now in its 58th year, returns to Clark Street in Andersonville. The festival features music, vendors, food, and free kids’ activities. Attendees are promised five stages with performances, traditional Swedish activities, and curated vendor booths. June 7-9. andersonville.org

3. Mural Magic Hits Uptown

The 5th Annual Uptown Art Walk will bring 50 new murals to the neighborhood’s growing art scene. The celebration includes a block party, procession, yoga, a movie at dusk, and more. Local businesses will host art exhibits and there will be activities for all ages. June 8. partners.exploreuptown.org

4. Bouquet of Fun

Schubas Tavern will transform into a botanical haven with its Garden Party Plant & Pop-Up Market. This daytime event promises an array of offerings from local Chicago plant shops, dispensaries, and ceramic artisans with the backdrop of ambient, folk, and psych tunes spun by DJs. Attendees can peruse the lush greenery and unique wares while indulging in food and drink specials. June 9. lh-st.com

5. Queer Joy and Skating

Bring out your roller skates to the 3rd Annual Pride Skate Party, hosted by Lighthouse Foundation of Chicagoland. The party will be held at the Dr. Martin Luther King, Jr. Roller Skating and Bowling Center. The event celebrates Black LGBTQ+ visibility, empowerment, and joy while dancing to summer beats and eating food. June 9. eventbrite.com