Chicago on the Cheap

Deals, discounts and free events in Chicago

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Free Millennium Park Summer Music Series

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

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

Free movies at Millennium Park

There's nothing better than watching a movie al fresco with a light picnic on the lush Millennium Park lawn. This Chicago summertime tradition is back with the Millennium Park Film Series, running from June 30 to August 18, 2026. Stroll into the Jay Pritzker Pavilion and watch classic, … [Read more...] about Free movies at Millennium Park

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

Free American Writers Festival

Celebrate the breadth and depth of the art of writing at the third annual American Writers Festival on June 6-7, 2026, at the American Writers Museum and the Harold Washington Library Center. The weekend of free programming will feature more than 90 writers. Sponsored by the … [Read more...] about Free American Writers Festival

Free Docent Led Tours at National Puerto Rican Museum

Discover the dynamic culture of Puerto Rico and Chicago's strong link to the island by taking a free docent-led tour of the National Museum of Puerto Rican Arts and Culture in the Humboldt Park neighborhood.  The tour is scheduled for May 30, 2026. Roam through the historic National … [Read more...] about Free Docent Led Tours at National Puerto Rican Museum

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

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

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