Piper’s Alley sits at the corner of North Avenue and Wells Street in Chicago’s Old Town, a compact retail and entertainment complex best known today as home to The Second City, the comedy theater that launched generations of sketch and improv talent. The name comes from Henry Piper’s 19th-century bakery on this block, and in the 1960s the passage became a counterculture arcade of boutiques and head shops. Visitors come here mainly for comedy, with shopping and dining as add-ons.
Inside, the brick corridors lead to Second City’s mainstage and e.t.c. stage, the larger UP Comedy Club, and the Second City Training Center, where students take improv and writing classes. The space once held the Pipers Alley movie theater, but that cinema closed years ago, and Second City converted much of the building into performance and classroom space. Street-level shops and restaurants along Wells and North Avenue fill out the block. Store listings change often, so check current tenants before you go.
Visitor Highlights & Practical Info
Book Second City tickets in advance, especially for Friday and Saturday evenings. Weeknight shows are easier to get. For a free option, stay after select performances for the late-night improv set. The CTA Brown and Purple Line stop at Sedgwick is a short walk away, and the #72 North Avenue bus stops at the door. Parking is available in the adjacent garage. Before or after a show, walk Wells Street for Old Town’s bars and restaurants, or head east to Lincoln Park and the free Lincoln Park Zoo. If you visit in June, expect larger crowds during the Old Town Art Fair.
