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
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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
Kentucky Derby Celebration at Time Out Market
Chicago loves celebrations. especially when there are cocktails and food involved. Enjoy drinks, eats, live music, a watch party and other entertainment at the free Kentucky Derby celebration on May 3, 2025, at Time Out Market Chicago. Deck yourself out in your best Kentucky Derby … [Read more...] about Kentucky Derby Celebration at Time Out Market
Buckingham Fountain Opening Day Events
Chicago's official start of the summer season always coincides with the spectacular splash of the first drops of the iconic Buckingham Fountain. This year's Switch on Summer Kick Off at Buckingham Fountain is set for May 10, 2025. Head to the fountain at 331 E. Randolph from 11:30 … [Read more...] about Buckingham Fountain Opening Day Events
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
