The essence of Summer in Chicago is listening to free concerts in the architectural beauty of Millennium Park. The beloved Millennium Park Summer Music Series soars from June 15 to August 6, 2026. The free concerts will run on Monday and Thursday evenings. The concerts feature a diverse range … [Read more...] about Free Millennium Park Summer Music Series
Music
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 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
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
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 10, 2026, and runs through August 15, 2026. Sit back in the beauty of the Pritzker Pavilion in Millennium … [Read more...] about Grant Park Music Festival
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
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
Maxwell Street Market
There's no Chicago market more iconic than Maxwell Street Market. This year, the market runs on select Sundays, May 17 through October 4, 2026, 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
Early Bird Chicago Boat Cruises for $20
It's that time of year! The season to enjoy Chicago views of gorgeous Lake Michigan has officially arrived and there's no better way to take in all the watery beauty than with a boat cruise. Chicago Party Boat is offering discounted Friday Night Skyline Cruises every Friday in May, May 1- 29, … [Read more...] about Early Bird Chicago Boat Cruises for $20
Free events at Daley Plaza under the Picasso
One of the joys of summer in Chicago is experiencing the eclectic cultural events at Daley Plaza. Under the shade of the Picasso sculpture, artists and performers from around the world sing, dance and present cultural ceremonies that supply an exciting assortment of cultural discoveries for … [Read more...] about Free events at Daley Plaza under the Picasso
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
