Things to Do in Chicago Under $20.

Chicago's longest-running outdoor farmers market held in the heart of The Loop beneath the iconic Picasso sculpture, featuring fresh local produce, baked goods, and lunch food trucks.

Authentic, high-octane live Chicago blues across two continuous stages running until 4:00 AM at the world-famous Lincoln Park blues institution operating since 1968.

Historic Uptown cocktail lounge and former Prohibition-era speakeasy hosting late-night live jazz jam sessions and quartet performances rolling until 3:30 AM.

Chicago's premier sustainable open-air farmers market connecting local Midwest farmers and artisan food makers with the community beneath Lincoln Park's tree canopy.

Award-winning choreographed fireworks lighting up Lake Michigan and the downtown skyline, free to view along the 3,300-foot pier promenade and surrounding lakefront parks.

Vibrant open-air Sunday community market along Milwaukee Avenue offering regional seasonal produce, local honey, artisan pastries, specialty coffees, and live street buskers.

Free live outdoor evening music and art gathering on the MCA sculpture garden terrace, featuring prominent Chicago musicians and museum gallery admission.

A celebrated Labor Day weekend Chicago tradition organized by DCASE and the Jazz Institute of Chicago, featuring world-renowned jazz artists and local Chicago legends across Jay Pritzker Pavilion and park lawns.

Chicago's legendary weekly Sunday LGBTQ+ underground house and disco party at Smartbar, featuring resident selector Derrick Carter, Michael Serafini, and Shaun J. Wright on the subterranean Funktion-One sound system.