Old Town occupies a stretch of Chicago’s North Side roughly between North Avenue and Armitage Avenue, centered on Wells Street. The neighborhood rebuilt after the Great Chicago Fire of 1871 and retains blocks of Italianate and Queen Anne row houses that make it one of the city’s best-preserved 19th-century streetscapes. It sits directly east of Lincoln Park and draws visitors for comedy, dining, nightlife, and architecture.
What is Old Town Chicago known for?
Old Town is best known as the home of The Second City, the legendary improvisational comedy theater on North Wells Street that launched careers including Bill Murray, Tina Fey, and Stephen Colbert, and for its intact blocks of post-Fire Victorian row houses that survived urban renewal pressures of the mid-20th century. The neighborhood also earned a national reputation during the 1960s folk revival when the Earl of Old Town and similar clubs on Wells Street hosted artists like John Prine and Steve Goodman.
Best things to do in Old Town
Attending a show at The Second City on North Wells Street is the single most distinctive Old Town experience, with mainstage revues and free late-night sets most Fridays and Saturdays. Additional worthwhile activities include:
- Walking the historic Crilly Court and Menomonee Street blocks to view preserved 1880s row houses
- Browsing the Old Town Art Fair, held annually in June in the residential streets around Lincoln Avenue and Wisconsin Street
- Visiting the Midwest Buddhist Temple on Menomonee Street, a community anchor since 1944
- Exploring the adjacent Lincoln Park Conservatory and the nearby North Pond area
Where to eat and drink in Old Town
Wells Street between North Avenue and Schiller Street contains the neighborhood’s densest concentration of restaurants and bars, ranging from longtime Chicago institutions to newer independent spots. Standout options include:
- Fireplace Inn on Wells Street, a longtime Chicago barbecue institution open since 1969
- Dinotto Ristorante on Wells Street for classic Italian in a long-running neighborhood setting
- Old Jerusalem Restaurant on North Wells, one of Chicago’s oldest Middle Eastern spots
- The bars and live-music venues clustered around the Wells and Division Street intersection
Where to walk in Old Town
The most rewarding Old Town walk runs north along Wells Street from North Avenue through the commercial strip, then turns west into the residential blocks of Menomonee Street, Eugenie Street, and Crilly Court to view the Victorian architecture before connecting south to the North/Clybourn area. A second route heads east on Wisconsin Street to the Lincoln Park lakefront path, offering views of North Pond and the Chicago skyline from the south end of the park.
How to get to Old Town Chicago
The most direct CTA access is the Brown Line or Purple Line to Sedgwick station on North Sedgwick Street, which places visitors one block from the core of Wells Street. Additional options include:
- CTA Red Line to Clark/Division station, a 10-minute walk east to Wells Street
- CTA Bus Route 36 (Broadway) and Route 72 (North) serve the neighborhood perimeter
- Divvy bike-share stations on Wells Street, Sedgwick Street, and North Avenue
Best time to visit Old Town
Late spring through early fall is the optimal time to visit Old Town, with the Old Town Art Fair in June drawing large crowds to the residential streets and outdoor dining on Wells Street at its peak from May through September. The Second City runs year-round, making winter visits practical for comedy-focused trips, and the quiet snow-covered Victorian streetscapes offer some of the city’s most atmospheric winter walks.
