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
Expired
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
Chicago Memorial Day Parade
The annual Chicago Memorial Day Parade and Wreath Laying Ceremony honors all men and women who made the ultimate sacrifice in defense of our country. This year's parade is scheduled for May 24, 2025. Head to Daley Plaza in the Chicago Loop to witness the moving Wreath Laying … [Read more...] about Chicago Memorial Day Parade
Mexico Fest at Navy Pier
The colors, music, dance and traditions of Mexico will light up Navy Pier during the exciting three-day events of Mexico Fest, scheduled for May 2-4, 2025. Dance along to noted dance troupes like Ballet Folklorico de Chicago and move to the rhythms of bands like Mariachi Estrellas de Chicago … [Read more...] about Mexico Fest at Navy Pier
Pullman Railroad Days
Explore the historic world of railcars and their glamorous history during Chicago's biggest rail-themed event, Pullman Railroad Days, on May 17 and 18, 2025, in the Pullman neighborhood. Step inside elegant Pullman railroad cars from the early 20th century and learn about passenger trains, … [Read more...] about Pullman Railroad Days
