Chicago on the Cheap

Deals, discounts and free events in Chicago

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Wicker Park Fest

Music lovers never want to miss the eclectic music line-up of Wicker Park Fest, scheduled for July 25-27, 2025. This popular neighborhood fest draws visitors from across the country who love cutting-edge sounds and funky arts and crafts vendors. Trendy Wicker Park has been the headquarters … [Read more...] about Wicker Park Fest

Chicago Gospel Music Festival

Enjoy the spirit-filled gospel music genre that was created in Chicago at the annual Gospel Music Festival on July 12, 2025, in Millennium Park. This beloved fest draws fans from all over the country to hear some of gospel's greatest voices at this free event. A cherished Chicago tradition … [Read more...] about Chicago Gospel Music Festival

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 Millenium Park Film Series, running from July 1 to August 19, 2025. Stroll into the Jay Pritzker Pavilion and watch … [Read more...] about Free movies at Millennium Park

1865 Fest Juneteenth Celebration

The annual 1865 Fest brings cultural family activities, live music, educational workshops, food and fun to Garfield Park for three days, June 18-20, 2025. Honoring the Juneteeth holiday that brought freedom to enslaved Americans two years after official emancipation in 1865, the free events … [Read more...] about 1865 Fest Juneteenth Celebration

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 Thursday, June 19, 2025.   Yoga, horseback riding, a farmers market, roller … [Read more...] about DuSable Museum Juneteenth Celebration

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 away from June 26 to August 7, 2025. The free concerts will run on Monday and Thursday evenings. The concerts feature a diverse … [Read more...] about Free Millennium Park Summer Music Series

Chicago Pride Fest

Chicago is home to the nation's first recognized LGBTQ community and the annual Chicago Pride Fest is one of its most anticipated community events. The fest returns on June 21-22, 2025, with three stages of music, vendors, food, drinks and fun. Kicking off the weekend before the Chicago Pride … [Read more...] about Chicago Pride Fest

Wells Street Art Festival

The historic Old Town neighborhood comes alive with the highly anticipated Wells Street Art Festival on June 14 and 15, 2025, in the heart of the landmark neighborhood Traditionally held on the second weekend in June, the fair features artists from all over North America, including painters, … [Read more...] about Wells Street Art Festival

Chicago Pride Parade

The Chicago Pride Parade is one of the oldest and largest pride parades in the country. Filled with floats, music, local celebrities and performers, Chicago's Pride Parade is one of the most anticipated events in Pride month. The 54th annual Chicago Pride Parade kicks off on June 29, … [Read more...] about Chicago Pride Parade

Free Tuesdays on the Terrace at the MCA

Chicago's acclaimed Museum of Contemporary Art is not just the place to view cutting-edge art pieces, it's also one of the most popular spots to hear free Summer jazz concerts. The beloved Tuesdays on the Terrace music series returns from June 24 to August 26, 2025.   Spreading a … [Read more...] about Free Tuesdays on the Terrace at the MCA

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