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
Chicago festivals
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
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
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
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
Belmont-Sheffield Music Fest
For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026. The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the … [Read more...] about Belmont-Sheffield Music Fest
Chicago Mayfest in Lincoln Park
Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood. This year's fest will kick off at Armitage and Sheffield and … [Read more...] about Chicago Mayfest in Lincoln Park
Sor Juana Festival Events
The annual Sor Juana Festival honors the historic Mexican writer, feminist and nun, Sor Juana Inés de la Cruz, with a dynamic line-up of artists, writers, filmmakers and singers at the National Museum of Mexican Art through April 29, 2026. Check out some of the exciting free … [Read more...] about Sor Juana Festival Events
