Chicago Event Calendar May 2025. Some of the top festivals to look forward to in chicago in 2025 include the chicago blues festival, taste of chicago, lollapalooza, chicago jazz festival, and chicago air and water show. Find out what's happening in chicago in may 2024, from festivals and concerts to brunch and bingo.

Browse by type of event, from live music and festivals to tours and sports, and book tickets or promote your own. Stay up to date on all of the events and shows happening in chicago, including exhibits, concerts, sports games, festivals, art shows, lectures, and children’s activities.