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
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Glenwood Sunday Farmers Market
Head to Rogers Park for one of the city's most vibrant and socially aware farmers' markets, Glenwood Sunday Farmers Market. The market runs on Sundays, from June 1 to October 26, 2025, from 9 am to 2 pm, at Glenwood and Morse Avenues. What makes this farmer's market stand out is its … [Read more...] about Glenwood Sunday Farmers Market
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
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
Summer Fireworks at Navy Pier
The spectacular fireworks display at Navy Pier is a much-anticipated Chicago hallmark. The twice-weekly Summer Fireworks show runs from May 24, 2025, through August 30, 2025. The dramatic fireworks spectacle features synchronized music and vivid bursts of color that can be viewed for miles. … [Read more...] about Summer Fireworks at Navy Pier
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
Discount Tickets for Saturday Night at the Zoo
Experience the sights and sounds of the zoo after dark, visiting animals and sipping cocktails at this adults-only evening event, Saturday Night at Lincoln Park Zoo on May 10, 2025. Stroll through the grounds of Lincoln Park Zoo at night and enjoy special after-hours viewing of the … [Read more...] about Discount Tickets for Saturday Night at the Zoo
Maxwell Street Market
There's no Chicago market more iconic than Maxwell Street Market. This year, the market runs on select Sundays, May 18 through October 5, 2025, 10 am -3 pm. Open since 1912, this bustling marketplace is much more than just a place to shop, it's a Chicago cultural mecca. Maxwell Street … [Read more...] about Maxwell Street Market
