Over 16 restaurants and two stages of live acts will commemorate the 28th anniversary of the Taste of Randolph on June 19-21, 2026. The highly anticipated festival features some of the best bites in the West Loop neighborhood. Expect to eat and dance your way through three days of events, … [Read more...] about Taste of Randolph Street
Entertainment
57th Street Art Fair
For art lovers, the Chicago summer season officially kicks off with Hyde Park's beloved 57th Street Art Fair. The 78th annual 57th Street Art Fair is the first major art fair of the season. It opens on June 6-7, 2026. Stroll through Hyde Park's tree-lined thoroughfares and browse a … [Read more...] about 57th Street Art Fair
Chicago Pride Fest
Chicago is home to the nation's first recognized LGBTQ community and the annual Chicago Pride Fest is one of its most anticipated community events. The fest returns on June 20-21, 2026, with three stages of music, vendors, food, drinks and fun. Kicking off the weekend before the Chicago Pride … [Read more...] about Chicago Pride Fest
Old Town Art Fair
Kick off your summer at one of the first art fairs in the country. Old Town Art Fair supplies art, music, food, a children's corner and a garden walk in the historic Old Town Triangle Historic District on June 13 and 14, 2026. Roam through the charming streets of Old Town and view the work of … [Read more...] about Old Town Art Fair
Puerto Rican Festival
The Humboldt Park neighborhood will celebrate 45 years of Puerto Rican history, culture and art with the annual Puerto Rican Festival on June 11-14, 2026. The four-day fest will fill Division Street with the sights and sounds of Puerto Rico. The music, dance, art and food of Puerto Rico … [Read more...] about Puerto Rican Festival
Chicago Blues Festival
Chicago is home to the largest free blues festival in the world and this much-anticipated event draws fans from all over the world to experience the influential art form that was nurtured in the city. The Chicago Blues Festival returns to Millennium Park from June 5-7, 2026. This free … [Read more...] about Chicago Blues Festival
Summer Fireworks at Navy Pier
The spectacular fireworks display at Navy Pier is a much-anticipated Chicago hallmark. The twice-weekly Summer Fireworks show runs from May 23, 2026, through September 5, 2026. The dramatic fireworks spectacle features synchronized music and vivid bursts of color that can be viewed for miles. … [Read more...] about Summer Fireworks at Navy Pier
Free Millennium Park Summer Music Series
The essence of Summer in Chicago is listening to free concerts in the architectural beauty of Millennium Park. The beloved Millennium Park Summer Music Series soars from June 15 to August 6, 2026. The free concerts will run on Monday and Thursday evenings. The concerts feature a diverse range … [Read more...] about Free Millennium Park Summer Music Series
Do Division Street Fest
Division Street in West Town comes alive with live music, food, boutique sales, fashion shows and family fun with the annual Do Division Street Fest on May 29-31, 2026. One of the most anticipated summer music fests, Do Division Street Fest serves up an astonishing selection of local … [Read more...] about Do Division Street Fest
Celebrate German Culture at Chicago Maifest
Welcome spring at the traditional German celebration of the season, Maifest Chicago. The 26th annual festival runs from May 29 -31, 2026, in the heart of Chicago's German community in Lincoln Square. Chow down on lots of German food and witness a traditional keg tapping, maypole dancing … [Read more...] about Celebrate German Culture at Chicago Maifest
Free movies at Millennium Park
There's nothing better than watching a movie al fresco with a light picnic on the lush Millennium Park lawn. This Chicago summertime tradition is back with the Millennium Park Film Series, running from June 30 to August 18, 2026. Stroll into the Jay Pritzker Pavilion and watch classic, … [Read more...] about Free movies at Millennium Park
Grant Park Music Festival
Enjoy the soothing strains of classical compositions as well as contemporary and Broadway tunes at the annual Grant Park Music Festival. This free summer concert series kicks off on June 10, 2026, and runs through August 15, 2026. Sit back in the beauty of the Pritzker Pavilion in Millennium … [Read more...] about Grant Park Music Festival
