The historic Old Town neighborhood comes alive with the highly anticipated Wells Street Art Festival on June 14 and 15, 2025, in the heart of the landmark neighborhood Traditionally held on the second weekend in June, the fair features artists from all over North America, including painters, … [Read more...] about Wells Street Art Festival
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Chicago Pride Parade
The Chicago Pride Parade is one of the oldest and largest pride parades in the country. Filled with floats, music, local celebrities and performers, Chicago's Pride Parade is one of the most anticipated events in Pride month. The 54th annual Chicago Pride Parade kicks off on June 29, … [Read more...] about Chicago Pride Parade
Puerto Rican Festival
The Humboldt Park neighborhood will celebrate 44 years of Puerto Rican history, culture and art with the annual Puerto Rican Festival on June 12-15, 2025. 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
Taste of Randolph Street
Over 16 restaurants and two stages of live acts will commemorate the 27th anniversary of the Taste of Randolph on June 13-15, 2025. 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
Lincoln Park Greek Fest
Enjoy the flavors, sounds and sights of Greek culture at the popular Lincoln Park Greek Fest on June 6-8, 2025. The annual cultural festival features authentic Greek food, music, dancing and a craft fair on the grounds of St. George Greek Orthodox Church Traditional Greek dishes … [Read more...] about Lincoln Park Greek 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 14 and 15, 2025. Roam through the charming streets of Old Town and view the work of … [Read more...] about Old Town Art Fair
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 11, 2025, and runs through August 16, 2025. Sit back in the beauty of the Pritzker Pavilion in Millennium … [Read more...] about Grant Park Music 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 5-8, 2025. This … [Read more...] about Chicago Blues 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 30- June 1, 2025. One of the most anticipated summer music fests, Do Division Street Fest serves up an astonishing selection of … [Read more...] about Do Division Street Fest
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
Mole De Mayo Festival in Pilsen
Head to the historic Mexican neighborhood of Pilsen to explore the joys of the traditional chocolate-based dish of mole, at the 16th annual Mole De Mayo fest from May 24-26, 2025. Restaurants and chefs will offer their best recipes for the rich sauce served over enchiladas or meats … [Read more...] about Mole De Mayo Festival in Pilsen
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 to June 1, 2025, 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 … [Read more...] about Celebrate German Culture at Chicago Maifest
