Dedicated Email - Friday - 08/28/2026 - DoStuff - Labor Day Guide 2026

Labor Day weekend is somehow one of the happiest and saddest weekends of the year. Chicago is packed with festivals, cruises, parties, and basically every excuse to stay out all weekend, but unfortunately, it also means summer is starting to wrap up. We're choosing to ignore that part for now. We can be sad on Tuesday… because we have 3 days of bad decisions ahead this Labor Day weekend. Music festivals, booze cruises, lakeside fireworks, and more are in our full guide.