Chicago’s iconic Old Town Art Fair proudly celebrates its 75th anniversary on June 14–15, 2025, with a historic first: a specially commissioned commemorative poster titled Soaring Around Old Town by acclaimed local artist Chuck Meyers.

A full-time Chicago painter for over 23 years and a Fair exhibitor for more than a decade, Meyers created the piece using a series of drone photography sessions throughout the Old Town Triangle neighborhood. His work, known for capturing the character of Chicago’s side streets, alleys, and transportation routes, offers a vibrant aerial portrait that honors the Fair’s deep-rooted connection to the city’s architecture and charm.

Since its founding in 1948, the Old Town Art Fair has become one of the oldest juried art fairs in the country, and a cultural highlight of Chicago’s summer festival season. While the Fair traditionally selects existing artwork from exhibiting artists for its annual poster, Soaring Around Old Town is the Fair’s first-ever commissioned poster, marking a visual milestone in its 75-year history. A complete archive of collectible posters is available online for art collectors and history buffs alike.

What to Expect at the 2025 Old Town Art Fair

This landmark year promises to be the Fair’s most festive yet, with over 230 artists from across the U.S. showcasing work in a wide variety of media: painting, sculpture, ceramics, photography, printmaking, glass, fiber, jewelry, and more. Each artist is hand-selected by a jury of art professionals, including gallery owners, curators, and established artists, ensuring exceptional quality and diversity.

Fair hours are:

• Saturday, June 14: 10am–7pm
• Sunday, June 15: 10am–6pm

Suggested entry donation is $12 for adults; children are admitted free. All proceeds directly support local schools, cultural organizations, and neighborhood preservation efforts through the Old Town Triangle Association, a nonprofit community organization.

A Weekend of Art, Music, Food & Garden Walks

Beyond visual arts, the Fair features:

• Live music on two stages
• Delicious food and drinks from beloved Chicago vendors
• A lively Children’s Corner with crafts and interactive activities
• The return of the Garden Walk, offering self-guided tours of over 50 hidden and historic gardens throughout the Old Town Triangle

The Fair annually attracts 30,000+ visitors, making it one of the most attended and beloved Chicago summer events.

This year’s Emerging Artist Booth has been awarded to Annabelle Sigmond, whose vivid paintings explore nature, geography, and climate change—adding a fresh and relevant voice to the Fair’s legacy.

Explore the Heart of Old Town

The Old Town Art Fair is a uniquely Chicago experience, combining world-class art with the intimate charm of a historic neighborhood. Visitors are encouraged to stroll the cobblestone streets, discover hidden gardens, and learn more about the storied architecture and community that has made Old Town a destination for decades.

Please note: The Old Town Art Fair is a separate event from the Wells Street Art Festival, which also takes place the same weekend.

For more information, visit oldtownartfair.org and follow @OldTownArtFair on Instagram and Facebook for updates and sneak peeks.

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