Old Town

Old Town is one of Chicago's most charming and historic pockets — a neighborhood of narrow streets, post-Fire workers cottages, and brick rowhouses centered on the Old Town Triangle, a designated historic district whose lanes feel closer to a 19th-century village than a modern city. St. Michael's Church, whose walls survived the Great Chicago Fire of 1871, still rings its bells over the neighborhood, and local tradition holds that you're in Old Town if you can hear them.

Wells Street is the commercial spine, lined with restaurants, bars, and shops — including Twin Anchors, the rib house pouring since 1932 — and it carries the neighborhood's most famous institution: The Second City, the comedy theater that has launched generations of performers since 1959. Zanies adds a second comedy stage down the street, and the Old Town Art Fair, running since the 1950s, takes over the Triangle every June as one of the oldest juried art fairs in the country.

Housing splits between the historic stock — cottages, rowhouses, and vintage walk-ups in and around the Triangle — and larger condo buildings and high-rises toward the eastern and southern edges, including Sandburg Village. Single-family homes in the Triangle are rare and held closely.

Lincoln Park — the park — begins immediately north and east, putting the zoo, North Avenue Beach, and the lakefront trail within a short walk. The Brown and Purple Lines stop at Sedgwick, the Red Line at Clark/Division is a walk southeast, and buses cover Wells, North, and LaSalle.

Old Town combines historic architecture, a walkable commercial street, and immediate park and lakefront access — in one of the smallest and most distinctive footprints on the North Side.

Old Town FAQ

Do you need a car in Old Town?

No — the Brown and Purple Lines stop at Sedgwick, the Red Line is a short walk, Wells Street covers daily errands, and the lakefront is walkable. Parking on the historic streets is tight if you keep a car.

What types of homes are in Old Town?

Historic workers cottages and rowhouses in the Old Town Triangle, vintage walk-ups and condos, and high-rise buildings including Sandburg Village toward the edges. Single-family homes in the Triangle rarely come to market.

What is Old Town known for?

The Second City comedy theater, the historic Old Town Triangle district, St. Michael's Church, the Wells Street restaurant corridor, and the Old Town Art Fair each June.

Old Town vs. Lincoln Park: what's the difference?

Old Town is smaller and sits at Lincoln Park's southern edge, sharing the park and lakefront. Lincoln Park is much larger with more single-family inventory and retail corridors; Old Town concentrates its historic charm and commercial life into a few blocks around Wells Street and the Triangle.