1. Sample the best from restaurant row
Randolph Street in the West Loop features some of Chicago's best restaurants, and at Taste of Randolph, you'll be able to try them all. Celebrating its 20th anniversary this year, the festival welcomes 20 restaurants, including Belly Q, Gus's Fried Chicken, Publican Quality Meats and many others. (Randolph St, Fri 5–10pm, Sat & Sun noon–10pm. Free)
Our city celebrates the LGBTQ community with food, drinks and entertainment that includes headliners such as Daya and American Idol alum Jordin Sparks. (Halsted St and Waveland Ave, Sat & Sun 10am. $10 donation)
3. Celebrate Puerto Rican heritage
The Fiesta Puertorriquenas party in Humboldt Park means summer has officially arrived. Sip cold drinks, eat hot food, dance to Latin music and hop on a carnival ride. (1400 N Sacramento Ave, Thurs–Sun. Free)
Vintage Garage packs every level of an Uptown parking garage with antique furniture and other treasures. For June, the theme focuses on vinyl records and, of course, Father’s Day. (5051 N Broadway, 10am–5pm. $5)
5. Listen to a seasoned storyteller
Settle in for a night of stories as everyone from live-lit regulars to first-timers tell true, hilarious stories from their own lives. Every event is loosely based on a theme and hosted by Jeremy Owens. This weekend, stories are themed in recognition of Pride month, and part of the proceeds benefit Women & Children's First Women's Voices Fund. (Women and Children First, 5233 N Clark St, 7pm. $10 suggested donation)