Chicago Event Calendar May 2026

Spring is in full swing in the vibrant city of Chicago, and there’s no shortage of exciting events happening throughout May 2026. From music festivals to food fairs, there’s something for everyone to enjoy in the Windy City this month.

Whether you’re a local looking for some fun activities or a visitor wanting to experience the best of Chicago, the event calendar for May is packed with options to keep you entertained. Get ready to mark your calendars and make the most of your time in this bustling metropolis.

Chicago Event Calendar May 2026

One highlight of the month is the Chicago Blues Festival, where you can groove to the soulful sounds of legendary blues musicians from around the world. This iconic event draws music lovers of all ages and is a must-visit for anyone in the city.

If you’re a foodie, be sure to check out the Taste of Chicago, where you can sample delicious dishes from the city’s top restaurants. From deep-dish pizza to gourmet hot dogs, this culinary extravaganza is a feast for the senses.

For art enthusiasts, the Chicago Contemporary Art Fair showcases the work of talented local and international artists. Explore cutting-edge installations, paintings, and sculptures that push the boundaries of creativity and expression.

As the month comes to a close, don’t miss the Memorial Day Parade, a patriotic celebration honoring the men and women who have served in the armed forces. Join the crowds lining the streets to pay tribute to our nation’s heroes and enjoy a day of community spirit.

With so much to see and do in Chicago this May, you’re sure to have a memorable time exploring the city’s vibrant culture and diverse offerings. From music to food to art, there’s something for everyone to enjoy in this dynamic urban hub. Plan your itinerary, gather your friends, and get ready for an unforgettable experience in the Windy City!