Summer in Chicagoland is truly the best. With over 20 street fairs, there is so much to celebrate, and there’s no better way to kick off the season than by attending an art-filled event.
Our favorite is the 57th Street Art Fair, which is considered the oldest juried art fair in the Midwest.

This historic 2-day Chicago festival is the top summer event
Established in 1948, this event is held annually in Hyde Park. This year marks its 79th anniversary, taking place in June and featuring around 200 artists, live music, and more. As the first major art fair of the season, it’s the perfect place to buy art, whether you’re a seasoned collector or new to the art scene.
Always held on the first full weekend of June, the fair offers a unique showcase of high-quality art and a vibrant community atmosphere, attracting about 20,000 visitors annually.
You can enjoy some of Chicago’s best blues music at Buddy Guy’s Legends Stage, meet friends, bring your family, and soak in the fun at this historic and welcoming event. All artists exhibiting at the fair will be present in their booths throughout the weekend to discuss their work.
The fair runs along 57th Street between Woodlawn and Kenwood Avenues and on Kimbark between 56th and 57th Streets.
When is the 57th Street Art Fair
Saturday, June 6: 11 AM – 6 PM
Sunday, June 7: 10 AM – 5 PM