The annual 1865 Fest brings cultural family activities, live music, educational workshops, food and fun to Garfield Park for two days, June 19-20, 2026. Honoring the Juneteenth holiday that brought freedom to enslaved Americans two years after official emancipation in 1865, the free events connect … [Read more...] about 1865 Fest Juneteenth Celebration
family friendly
Chicago Full Moon Fire Jam
The full moon is celebrated in many ways in different cultures but in Chicago, fire dancers and percussion are the highlights of the annual summer Full Moon Jam. Glowing along the shores of Lake Michigan, this year's full moon jams will take place on June 13, June 29, July 4, July 29, … [Read more...] about Chicago Full Moon Fire Jam
Live on the Lake Free Summer Concerts
Music fans can enjoy the beauty of lakeside views as well as live melodies during the free weekly Live on the Lake summer concert series at the Navy Pier Beer Garden. every weekend, through September 7, 2026. Grab a cold one from Tangled Roots Brewery or nibble on nachos or a brat while … [Read more...] about Live on the Lake Free Summer Concerts
DuSable Museum Juneteenth Celebration
DuSable Black History Museum and Education Center celebrates Juneteenth, the oldest nationally recognized commemoration of the ending of slavery in the U.S., with an all-day Juneteenth Celebration on Friday, June 19, 2026. Yoga, horseback riding, a farmers' market and special … [Read more...] about DuSable Museum Juneteenth Celebration
57th Street Art Fair
For art lovers, the Chicago summer season officially kicks off with Hyde Park's beloved 57th Street Art Fair. The 78th annual 57th Street Art Fair is the first major art fair of the season. It opens on June 6-7, 2026. Stroll through Hyde Park's tree-lined thoroughfares and browse a … [Read more...] about 57th Street Art Fair
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 13 and 14, 2026. Roam through the charming streets of Old Town and view the work of … [Read more...] about Old Town Art Fair
Puerto Rican Festival
The Humboldt Park neighborhood will celebrate 45 years of Puerto Rican history, culture and art with the annual Puerto Rican Festival on June 11-14, 2026. The four-day fest will fill Division Street with the sights and sounds of Puerto Rico. The music, dance, art and food of Puerto Rico … [Read more...] about Puerto Rican Festival
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
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
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
Celebrate Spring with a Bonfire at Andersonville’s Valborg
Join the Swedish tradition of welcoming spring and banishing winter with a roaring bonfire, music, poetry, food and dance at the second annual Valborg in the Andersonville neighborhood on April 30, 2026. Sit around the bonfire and toss the worries you've written down into the flames to kick … [Read more...] about Celebrate Spring with a Bonfire at Andersonville’s Valborg




















Chicago on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at 