Randolph Street Market

By CGN Staff

Chicago’s summer art fair season is about to begin, bringing weekends filled with artists, vintage finds, live music, and neighborhood traditions across the city. The fairs of summer are distinct from international gatherings like EXPO Chicago, as many are focused on local artists selling approachable art and crafts, and casual attendees can enjoy family friendly activities, food trucks and music.

The season unofficially kicks off Memorial Day weekend with the return of the Randolph Street Market in the West Loop. Founded in 2003 by entrepreneur Sally Schwartz, the market helped pioneer Chicago’s large-scale vintage and antique market scene and has since become a destination for designers, collectors, and treasure hunters from across the Midwest. The popular “Garden Party” market, May 23–24, brings together hundreds of vendors offering antiques, vintage fashion, art, jewelry, home décor, and global goods, all with a distinctly European flea market atmosphere. An additional market takes place July 25th and 26th.

57th Street Art Fair

Hyde Park hosts the 57th Street Art Fair on June 6–7. Established in 1948 by a group of Hyde Park artists and neighborhood residents, the fair is widely recognized as the oldest juried art fair in the Midwest and one of the oldest continuously running art fairs in the country. Now in its 79th year, the event features nearly 200 artists alongside live music, food vendors, and family programming. Its relaxed neighborhood setting and longstanding commitment to supporting independent artists continue to make it a favorite destination for collectors. You can also listen to some of Chicago's best Blues music at the Buddy Guy's Legends Stage.

Several lakefront festivals produced by Amdur Productions are also planned for June and July. The Gold Coast Art Fair returns to Grant Park June 20–21, showcasing artists from around the country in one of the city’s most high-profile outdoor settings. In July the Millennium Art Festival transforms Michigan Avenue into an open-air gallery featuring paintings, sculpture, jewelry, photography, and live entertainment.

Old Town Art Fair

The second weekend of June is especially busy with both the Old Town Art Fair and the Wells Street Art Festival drawing thousands of visitors to Old Town. The Old Town Art Fair is particularly known for its lineup of juried artists, charming garden walk through the neighborhood’s historic homes, and lively social atmosphere that blends serious collecting with a summer street festival feel. Nearby, the Wells Street Art Festival adds live music, food, and a more casual party atmosphere stretching along Wells Street. While the traffic can be a headache, the art + party mix is popular year after year.

At these markets and fairs, visitors can find affordable art made by artists working today. Each event offers an opportunity to engage with creativity and to support individual artists. Throughout the summer, art fairs and neighborhood festivals continue nearly every weekend across Chicago and the suburbs, offering collectors and casual visitors countless opportunities to discover emerging artists and enjoy the city’s vibrant outdoor arts scene.

For a full list of summer fairs, gallery events, and exhibitions, visit CGN’s calendar of events.