Jack’s Pumpkin Pop-Up
Kicking off it’s opening weekend, Jack’s Pumpkin Pop-Up is back on its two-acre site just west of Goose Island, offering all the fun of fall without the trip to the suburbs. You’ll find a sprawling corn maze, 10,000 pumpkins, axe throwing, carnival games, food trucks, and glowing orange lights. General admission gets you into the action, but you can upgrade to snag a pumpkin, enjoy a drink at one of the bars, or try axe throwing.
Race for the River 5K & Festival
Run alongside the Chicago River in this 5K that follows the North Shore Channel Trail. After crossing the finish line, stick around for river-themed activities, drinks, and snacks. Your registration includes a commemorative shirt and a drink ticket. Proceeds support Friends of the Chicago River, an organization dedicated to preserving and restoring the Chicago-Calumet River system.
Englewood Jazz Festival
This year’s Englewood Jazz Festival celebrates 25 years of spotlighting talent cultivated by the festival and Live the Spirit Residency. The three-day event features performances from artists like Nicole Mitchell, Jeremiah Collier/JC and the REUP, Corey Wilkes, Junius Paul, the Greg Ward Quartet, Jahari Stampley and The Young Masters, along with an encore presentation of Paul Robeson: Man of the People.
Chicago Live!
Navy Pier’s performing arts festival returns, showcasing over 100 local artists with performances spread across five stages. The weekend includes a mix of Chicago favorites like The Joffrey Ballet, Second City, and Blue Man Group, alongside special appearances from stars like RuPaul’s Drag Race alum Ginger Minj and Tony-nominated Felicia Fields. You’ll also discover fresh, up-and-coming talent. The highlight of the event is a free solo acoustic set by Wilco’s Jeff Tweedy on Saturday.