Music fans can enjoy the beauty of lakeside views as well as live melodies during the free weekly Live on the Lake summer concert series at the Navy Pier Beer Garden. every weekend, through September 7, 2026. Grab a cold one from Tangled Roots Brewery or nibble on nachos or a brat while … [Read more...] about Live on the Lake Free Summer Concerts
live music
DuSable Museum Juneteenth Celebration
DuSable Black History Museum and Education Center celebrates Juneteenth, the oldest nationally recognized commemoration of the ending of slavery in the U.S., with an all-day Juneteenth Celebration on Friday, June 19, 2026. Yoga, horseback riding, a farmers' market and special … [Read more...] about DuSable Museum Juneteenth Celebration
Taste of Randolph Street
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
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
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
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
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
Things To Do In Chicago in May
With spring weather warming up more consistently and the lakefront thawing into lovely aquamarine waves, May is a favorite time to explore Chicago before the large summer tourist crowds arrive. Consider these free or low-cost activities for your Chicago May adventures. Besides the essential … [Read more...] about Things To Do In Chicago in May
