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
live music
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
Free Music Frozen Dancing Block Party
There's no more quintessential Chicago winter music festival than the annual Music Frozen Dancing block party outside the iconic Empty Bottle indie music venue. This year's frigid fun kicks off on February 21, 2026. Grab your warmest puffer jacket and head to Logan Square for the best outdoor … [Read more...] about Free Music Frozen Dancing Block Party
Free Black History Concert at Auditorium Theatre
Experience the musical journey of the Black Diaspora during the thrilling Black History Month concert series: "Black History Concert Series: Voices of 'Ase: Afrofuturism II" by Uniting Voices Choir on February 24, 2026. The free concerts honor the tradition of Afrofuturism, which … [Read more...] about Free Black History Concert at Auditorium Theatre
New Year’s Rockin’ Eve in Chicago
For the first time ever, the iconic Dick Clark's New Year's Rockin' Eve will feature Chicago's midnight countdown on the country's most-watched New Year's Eve Broadcast. Chicago will host the free New Year's Eve countdown on the Chicago Riverwalk on December 31, 2025, kicking off at 7 … [Read more...] about New Year’s Rockin’ Eve in Chicago
Millennium Park Holiday Sing-Alongs
Celebrate the season with festive live concerts every Friday with the Millennium Park Holiday Sing-Along starting on December 5, 12 and 19, 2025. Join a diverse group of choirs and ensembles as they light up the park with music. The holiday Sing-Along kicks off on Fridays from 6-7 pm, right … [Read more...] about Millennium Park Holiday Sing-Alongs
