Nestled just north of Chicago’s bustling downtown and bordered by North Avenue, Clark Street, and Wells Street, Old Town feels like a living time capsule—an inviting mix of storied history, charming architecture, verdant parks, and a community spirit that thrives even as the city continues to grow and change. Whether you’re wandering its iconic streets on a lazy afternoon, enjoying the shade in Seward Park, or catching a show at the legendary Second City, Old Town is a place where the past and present meet in the most delightful way.
The Origins of Old Town
The roots of Old Town stretch all the way back to the mid-19th century, in an area once designated as the "Cabbage Patch" due to its large population of German immigrants who tilled the land and grew vegetables for the expanding city. These early settlers chose the low-lying spot west of Lincoln Park—a patchwork of vegetable gardens, tiny cottages, and narrow, winding streets—to plant their roots.
Old Town’s earliest residents shaped the neighborhood’s quirky, organic street grid, which stands in sharp contrast to Chicago’s rational street system. Today, you can still meander the bends of streets like Menomonee, North Park, and Eugenie—each a reminder of Old Town’s pre-Great Chicago Fire maze.
How Old Town Got Its Name
Officially known as the Near North Side, the area didn’t take on the name “Old Town” until the 1940s. During World War II, a group of neighbors banded together for civil defense drills and needed a way to define their section of the city. They dubbed the area “Old Town Triangle”—a nod to the neighborhood's distinctive shape and historic flavor.
The moniker stuck, spurred on by a rising preservation movement in the post-war years, and came to embody the neighborhood’s appreciation for old-world character and community.
Key Historical Milestones
- The Great Chicago Fire (1871): While much of the city burned, Old Town’s boundaries—especially north of North Avenue—managed to survive relatively unscathed. Many original Victorian-era cottages and rowhouses remain, particularly along Crilly Court, one of Chicago’s most picturesque blocks.
- 1960s Urban Revitalization: Old Town emerged as an epicenter of Chicago’s bohemian culture. The neighborhood became synonymous with the counterculture, artists, and progressive thinkers, drawing young residents to its cozy, affordable apartments and storefronts.
- Old Town Art Fair: Born in 1949, the Art Fair started as a way for local artists to show and sell their work while raising funds to beautify the community. Held annually along the leafy streets of the Old Town Triangle, it now attracts tens of thousands each June and is one of Chicago’s cherished summer traditions.
Notable Landmarks and Buildings
Old Town is blessed with some of the city’s oldest and most unique architecture.
- St. Michael’s Church (1633 N Cleveland Ave): One of the few buildings to survive the Great Chicago Fire, this towering, Gothic Revival masterpiece remains an anchor of the community and is visible from many vantage points.
- Crilly Court (Between Wells and St. Paul): Step onto this quiet, brick-lined street to view some of Chicago’s most well-preserved 19th-century homes—each built in Italianate or Queen Anne styles.
- Second City (1616 N Wells St): Legendary as the birthplace of improvisational comedy, Second City has launched the careers of countless comedic legends, including Tina Fey, Bill Murray, and Steve Carell. The laughter and creative energy here are essential to Old Town’s quirky, artistic soul.
- The Old Town Ale House (219 W North Ave): For decades, this classic Chicago tavern has served as a gathering place for artists, journalists, and neighbors. Its walls, filled with irreverent portraits, and its storied clientele are legendary in their own right.
Parks, Streets, and Spaces
What makes Old Town particularly distinctive is how it weaves city life with pockets of calm and greenery.
- Seward Park (375 W Elm St): This beloved community hub offers basketball courts, a playground, and wide-open lawns, providing sanctuary for children and adults alike.
- Wells Street: Once a humming thoroughfare for horse-drawn wagons, today Wells bustles with restaurants, boutiques, and live music venues. Strolling this street is a Chicago must, whether you’re grabbing a morning coffee or enjoying a late-night jazz set.
- Old Town Triangle: The heart of the neighborhood, bounded by North Avenue, Clark Street, and the former Ogden Avenue, is distinctive for its maze-like, pre-Fire street plan.
Evolution Through the Decades
Old Town’s history is a story of transformation and resilience. After the bohemian heyday of the 1960s and 70s, the neighborhood experienced waves of gentrification. Rising property values brought restoration efforts, helping save dozens of aging homes from demolition. Yet, Old Town has managed to balance this new investment with a strong preservationist ethos—one that still protects historic buildings and encourages a sense of continuity.
Institutions such as the Old Town Triangle Association work tirelessly to maintain the neighborhood’s character. And each summer, as neighbors and visitors flock to the Old Town Art Fair or browse the Green City Market, you’ll find that the area’s creative and communal spirit is very much alive.
Why Old Town Captivates
Ask any longtime resident what makes Old Town special, and you’ll hear a common refrain: It’s all about the people, the stories, and the sense of belonging. Children race down leafy sidewalks. Artists paint in sun-dappled studios. Friends linger on brownstone stoops as church bells echo across the Triangle.
With its rich tapestry of history, preserved architecture, and community warmth, Old Town continues to welcome newcomers without ever losing sight of its roots. Here, the city’s past and present aren’t in competition—they’re in joyous conversation, every day.