Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.

One of the most unique events of the season is returning this year. The Midway 5K Run & Walk is back to support Special Children’s Charities fund programming for children and adults with disabilities across Chicago. Participants can run or walk the course, which takes place on the airfield at Midway Airport. The main event is followed by a race for kids aged 5-10.

Send summer off with a bang at this indoor/outdoor music and arts festival in suburban Bridgeview (7337 W 100th Pl, Bridgeview, IL, 60456), which has been held on the last Saturday of the summer since its debut in 2024. This year, EDM duo Big Gigantic headlines, alongside Saxsquatch, Henry Fong, The Sponges and more. Check out the full lineup here.