Old Town Art Fair 2026

Old Town's other history

The Triangle's frame houses survived because they sat just past the 1871 fire's northern reach in places, and the neighborhood later became a center of Chicago's folk music and comedy scenes — the Old Town School of Folk Music began here and Second City opened on Wells Street in 1959.

Walking the fair means walking past that history block by block. Take the side streets rather than the main artery; the best gardens and the oldest houses are off the primary route.

How to buy from an artist

Most first-time buyers assume the sticker is fixed and walk away. Artists at juried fairs generally expect a conversation: ask about the process, the edition size, whether smaller works exist, and how framing or shipping is handled.

Prints and smaller studies are how most collections start. A signed original print from a working artist at this fair often costs less than a mass-produced piece from a furniture store, and it comes with a name you can follow.

Take a card even when you do not buy. Artists rotate through the same regional fair circuit, and the piece you hesitated on is frequently still available a month later.

What the fair is

The Old Town Art Fair is a juried outdoor art fair held on the tree-lined streets of the Old Town Triangle, where roughly 250 artists selected from a national applicant pool exhibit painting, sculpture, ceramics, printmaking, jewelry, photography and mixed media.

Juried is the operative word. Artists apply and are selected by panel, so the quality floor is considerably higher than at a general craft market, and prices reflect original work rather than reproductions.

Why it has lasted since 1950

The fair began as a neighborhood fundraiser and has run for over seven decades, making it one of the oldest juried outdoor art fairs in the country. Proceeds support neighborhood improvement and local arts and community organizations.

The setting explains the endurance. The Old Town Triangle survived the 1871 Chicago Fire in part and kept its nineteenth-century frame houses and narrow streets — an unusual streetscape for a city that rebuilt most of itself in brick.

The garden walk

Running alongside the fair, the garden walk opens private residential gardens in the Triangle to ticket holders. These are working city gardens behind century-old houses, and access is otherwise impossible.

For many regulars the garden walk is the reason to buy the admission rather than the art.

• Admission is a suggested donation at the gate that supports the neighborhood organizations
• Saturday morning is the calmest window; Sunday afternoon the busiest
• Bring a card — most artists take payment digitally, and originals are not impulse-priced
• Ask artists about shipping if you are visiting; most will arrange it

Getting to Old Town

The Brown and Purple Lines stop at Sedgwick, a few blocks from the fair, and the Red Line at North/Clybourn is a walk east. CTA buses 22 Clark, 36 Broadway and 72 North serve the perimeter.

Street parking in Old Town is permit-restricted and effectively unavailable on fair weekend. Transit or a rideshare drop at the edge of the footprint is the practical approach.

What else is nearby

Lincoln Park, the free Lincoln Park Zoo and the Conservatory are a short walk north. Wells Street's restaurants and Second City are inside the neighborhood, and the lakefront path is ten minutes east.

The Wells Street Art Festival runs on a separate weekend nearby with a different, less formal character — worth knowing so you do not confuse the two.

More Chicago art markets

The city's art and maker calendar includes the Chicago Artisan Market, the Chicago Makers Market, the Black Girl Art Show and neighborhood gallery nights in Pilsen and the West Loop.

Eventchaser lists Chicago art and market dates on our culture page.