Wicker Park Fest

When it comes to street festivals, the annual Wicker Park Fest is usually one of the season's largest (and most crowded) events, attracting thousands of people to a stretch of Milwaukee Avenue that's crowded with bars, chain restaurants, boutiques and shoe stores. Jam out to live music—you'll also find plenty of food from local vendors, well-stocked beer tents, sales at surrounding shops and a dedicated kids area.