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
live music
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 7-8, 2025. Stroll through Hyde Park's tree-lined thoroughfares and browse a … [Read more...] about 57th Street Art Fair
Free Tuesdays on the Terrace at the MCA
Chicago's acclaimed Museum of Contemporary Art is not just the place to view cutting-edge art pieces, it's also one of the most popular spots to hear free Summer jazz concerts. The beloved Tuesdays on the Terrace music series returns from June 24 to August 26, 2025. Spreading a … [Read more...] about Free Tuesdays on the Terrace at the MCA
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
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
Randolph Street Market
In honor of the spring season, Chicago's signature open-air market, the Randolph Street Market, is hosting its annual spring opening with vintage treasures, live bands, food and fun on May 24-25, 2025, in the West Loop. Celebrating 22 years, the Randolph Street Market Festival features an … [Read more...] about Randolph Street Market
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
Ina Mae Tavern Music Festival
Celebrate the high-energy spirit of New Orleans with live blues, jazz and dance rhythms, Creole food, cocktails and a joyful time in the Wicker Park neighborhood at Ina Mae Tavern Music Festival on April 24-27, 2024. Prepare for a non-stop four-day party at Ina Mae's Music Festival, which … [Read more...] about Ina Mae Tavern Music Festival
