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
Music
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
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
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
Chicago Mayfest in Lincoln Park
Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 28th annual edition continues the tradition from May 16-18, 2025, in the Lincoln Park neighborhood. This year's fest will kick off at Armitage and Sheffield and … [Read more...] about Chicago Mayfest in Lincoln Park
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
Belmont-Sheffield Music Fest
For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 23-25, 2025. The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the … [Read more...] about Belmont-Sheffield Music Fest
