Welcome to Old Town: Where Historic Charm, Cobblestone Streets, and Timeless Chicago Character Come Alive

Tucked in the heart of the Near North Side, Old Town is one of Chicago’s most picturesque and enduring neighborhoods — a place where 19th-century architecture, cultural legacy, and village-like charm blend seamlessly with modern city life. Bounded by North Avenue to the south, Armitage Avenue to the north, Wells Street to the east, and Halsted Street to the west, this storybook enclave feels like a hidden gem just steps from the Loop, Lincoln Park, and bustling North Avenue.

Known for its gas-lit cobblestone streets, beautifully preserved Victorian homes, and deep-rooted community spirit, Old Town is more than a neighborhood — it’s a living piece of Chicago history.

🏘️ A Neighborhood Preserved in Time

Old Town is home to one of the largest concentrations of pre-Civil War homes in Chicago — many of which survived the Great Chicago Fire of 1871. Its tree-lined streets are lined with:

Restored Italianate, Gothic Revival, and Queen Anne-style mansions
Cozy cottages and carriage houses with ivy-covered walls
Historic row houses and courtyard buildings that exude old-world elegance

The Old Town Triangle, the neighborhood’s historic core, is a designated Chicago Landmark District, where strict preservation rules ensure that the area’s architectural beauty remains intact for generations.

It’s a place where front porches are used, gardens are meticulously kept, and holiday decorations go up on time — a true neighborhood of pride and permanence.

🎭 The Birthplace of Chicago Theater

Old Town is legendary for its cultural contributions, most notably as the birthplace of The Second City — the world-famous improvisational theater that launched the careers of comedy giants like Bill Murray, Tina Fey, Steve Carell, and John Belushi.

Founded in 1959 in a former rat-infested nightclub on Wells Street, The Second City became a global phenomenon and put Old Town on the map as a hub of creativity, satire, and innovation.

Today, the neighborhood still pulses with artistic energy:

The Old Town School of Folk Music — one of the largest nonprofit music schools in the U.S., offering classes, concerts, and community events in a stunning riverfront campus
Intimate live music venues, poetry slams, and indie theater performances
Annual events like the Old Town Art Fair (one of the nation’s largest), Tree Lighting Ceremony, and Oktoberfest

It’s a neighborhood where art isn’t just displayed — it’s lived.

🛍️ Charming Shops, Cozy Eateries & Local Flair

Old Town’s commercial heart — Wells Street, North Avenue, and Menomonee Street — offers a mix of boutique charm and neighborhood convenience:

Independent bookstores, gift shops, and art galleries
Cozy cafes, wine bars, and farm-to-table restaurants
Family-run bakeries, florists, and specialty grocers

You won’t find chain stores or flashy developments here. Instead, you’ll discover authentic, locally owned businesses that serve residents and visitors alike — the kind of places where the owner remembers your name.

🌳 Green Space & Lakefront Access

Despite its urban setting, Old Town enjoys access to beautiful outdoor spaces:

Lincoln Park — just blocks east, offering 1,200 acres of green space, the Lincoln Park Zoo, and the Lakefront Trail
Couch Park — a small but beloved neighborhood green space with a playground and seasonal events
The Chicago Riverwalk and North Avenue Beach are just minutes away

Whether you're jogging along the lake, biking to downtown, or enjoying a quiet evening by the river, nature is never far.

🚇 Connected, Walkable, and Central

Old Town is one of the most transit-friendly and walkable neighborhoods in Chicago:

Served by the CTA Brown, Red, and Purple Lines at Fullerton and Sedgwick stations
Multiple bus routes: #22 Clark, #36 Broadway, #73 Armitage
Easy access to I-90/94 (the Kennedy Expressway)

You’re just:
📍 10 minutes from the Loop
📍 5 minutes from Lincoln Park and DePaul University
📍 15 minutes from O’Hare Airport

Many residents live car-free, thanks to the area’s high walk and transit scores.

❤️ A Community That Stays Together

Old Town isn’t just beautiful — it’s deeply connected.

The Old Town Triangle Association has protected the neighborhood’s character for over 60 years
Block clubs, school councils, and civic groups keep the area clean, safe, and engaged
Families, empty nesters, and young professionals coexist in a community that values stability, tradition, and inclusion

It’s a place where you wave to your neighbor, attend a folk concert on the river, and feel like you truly belong.