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 29-31, 2026. One of the most anticipated summer music fests, Do Division Street Fest serves up an astonishing selection of local … [Read more...] about Do Division Street Fest
live music
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 -31, 2026, 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 dancing … [Read more...] about Celebrate German Culture at Chicago Maifest
Andersonville Midsommarfest
One of the most beloved summer events is when the Andersonville neighborhood celebrates its Swedish heritage and culture with the 60th annual Andersonville Midsommarfest, from June 12 through June 14, 2026. One of Chicago's oldest and most anticipated street festivals, Andersonville … [Read more...] about Andersonville Midsommarfest
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
Randolph Street Market Festival
One of the most beloved events of the early summer season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on May 23-24, 2026, in the West Loop. Celebrating 23 years, the Randolph Street … [Read more...] about Randolph Street Market Festival
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 22-24, 2026. The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the … [Read more...] about Belmont-Sheffield Music Fest
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 29th annual edition continues the tradition from May 15-17, 2026, 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
Sor Juana Festival Events
The annual Sor Juana Festival honors the historic Mexican writer, feminist and nun, Sor Juana Inés de la Cruz, with a dynamic line-up of artists, writers, filmmakers and singers at the National Museum of Mexican Art through April 29, 2026. Check out some of the exciting free … [Read more...] about Sor Juana Festival Events
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through June 24, 2026, at 8:00 pm, the Old Town School of Folk Music will host a free concert series, World Music Wednesdays, featuring musicians from all around the world. Culture and countries represented … [Read more...] about Free World Music Wednesday Concerts
Chicago Hosts International Jazz Day with Free Concerts and Events
Commemorating 15 years of jazz music's role in fostering peace and intercultural dialogue, International Jazz Day is celebrated in 190 countries around the globe. On April 30, 2026, Chicago will host an all-star global concert, directed by the city's own and International Jazz Day founder, Herbie … [Read more...] about Chicago Hosts International Jazz Day with Free Concerts and Events
Chicago’s St. Patrick’s Day Events
Chicago dives deep into St. Patrick's Day festivities; this is a city that definitely believes in the green. Celebrating Irish heritage in Chicago means not just one, but three parades, kicking off on March 14-15, 2026. The granddaddy of them all, the downtown … [Read more...] about Chicago’s St. Patrick’s Day Events
St. Patrick Day Fest at Irish American Heritage Center
Celebrate St. Patrick's Day with two days of Irish music, dance, food and drink during the annual St. Patrick's Day Fest at the Irish American Heritage Center in the Mayfair neighborhood on March 14 and 15, 2026. The Irish American Heritage Center hosts the biggest St. Pat's Day party … [Read more...] about St. Patrick Day Fest at Irish American Heritage Center
