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
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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
Andersonville Midsommarfest
One of the most beloved summer events is when the Andersonville neighborhood celebrates its Swedish heritage and culture with the 60th annual Andersonville Midsommarfest, from June 12 through June 14, 2026. One of Chicago's oldest and most anticipated street festivals, Andersonville … [Read more...] about Andersonville Midsommarfest
Free American Writers Festival
Celebrate the breadth and depth of the art of writing at the third annual American Writers Festival on June 6-7, 2026, at the American Writers Museum and the Harold Washington Library Center. The weekend of free programming will feature more than 90 writers. Sponsored by the … [Read more...] about Free American Writers Festival
Free Docent Led Tours at National Puerto Rican Museum
Discover the dynamic culture of Puerto Rico and Chicago's strong link to the island by taking a free docent-led tour of the National Museum of Puerto Rican Arts and Culture in the Humboldt Park neighborhood. The tour is scheduled for May 30, 2026. Roam through the historic National … [Read more...] about Free Docent Led Tours at National Puerto Rican Museum
