Old Town
Landmark Cottages, Second City, Lincoln Park
MEDIAN: $431,500
Get to know Old Town
Old Town is one of Chicago's oldest neighborhoods and one of its most charming: a tight grid of cottages, rowhouses and tree-lined lanes centered on Wells Street at North Avenue. It sits just north of the Gold Coast, with Lincoln Park and the lake to the east and the Loop a short ride south.
People move here for the mix. You get historic homes on quiet side streets, a main street full of restaurants and comedy clubs, and the zoo and the beach within walking distance.
The neighborhood was settled by German immigrants in the 1850s and rebuilt after the Great Chicago Fire. Its oldest streets predate the city grid, so they still run at angles, which is part of what makes an ordinary walk here feel like a discovery.
Why People Love Old Town
Residents describe Old Town the same way: a real neighborhood with the city's best amenities around the corner.
It feels like home, not downtown. Residents say Old Town has a more residential feel than River North or the Gold Coast while staying a walk from the Magnificent Mile.
The park and the lake are right there. Lincoln Park, its free zoo and North Avenue Beach are all a short walk east, along with the Lakefront Trail.
Dinner never gets boring. Reviewers rave about the restaurants and pubs, from old-school rib joints to BYOB sushi, and Wells Street keeps adding more.
Comedy is a neighborhood institution. The Second City has called Wells Street home for decades, and its alumni turn up at the bars nearby.
Neighbors and businesses pull together. Residents say local businesses team up on neighborhood events, and the Old Town Triangle Association runs one of the oldest art fairs in the country.
Getting around is easy. The Sedgwick Brown and Purple Line stop sits in the middle of the neighborhood, the Clark/Division Red Line is at its southern edge, and buses run along North Avenue, Clark and LaSalle.
Want to live in Old Town?
John will match you with a Chicago agent who knows these blocks, at no cost to you.
What to do in Old Town
In Old Town, a single day can take you from a 19th-century side street to the zoo to a front-row seat at Second City.
Start with a wander through the Old Town Triangle. Crilly Court, Fern Court and Menomonee Street are lined with worker cottages and rowhouses, and St. Michael's Church rises above the rooftops just as it did after the Fire. Then cross into Lincoln Park for the free zoo, or keep going to North Avenue Beach.
Wells Street is the everyday main street. Pick up seasonings at The Spice House, browse the boutiques and grab lunch on a patio. Residents also point to an unexpected find a few blocks west: the Midwest Buddhist Temple, a beautifully designed and welcoming landmark.
Evenings come with history. Twin Anchors serves ribs that locals call the best in the city, the Old Town Ale House has poured drinks since 1958 and Marge's Still still serves from its original wooden bar. Kamehachi, a longtime sushi favorite, sits on Wells. Then catch a show at The Second City.
The neighborhood's big weekend comes each June. The Old Town Art Fair fills the Triangle with more than 200 juried artists, live music and a Garden Walk through dozens of private gardens, and the separate Wells Street Art Festival runs the same weekend just south.
Housing Types & Architecture
Old Town is a historic-homes neighborhood with condos layered in: cottages and rowhouses on the side streets, vintage three-flats in between and newer high-rises at the edges.
The Old Town Triangle, north of North Avenue, is a Chicago Landmark District. After the Fire, residents rebuilt with small frame worker cottages until the city banned wood construction; later homes went up in brick and stone, along with rowhouses and apartment buildings. The district's exteriors are protected, so the streetscape looks much as it did more than a century ago.
Crilly Court is a showpiece. A developer built rowhouses and apartment buildings there in the 1880s and 1890s, and named four of them after his children, with the names carved above the doors.
Beyond the Triangle, you'll find three-flats, townhomes and single-family homes, plus the Sandburg Village towers and newer high-rises along the neighborhood's southern and western edges. Condos in those buildings are the most common way in.
The quick read: a strong fit if you want a historic home or a vintage condo on a walkable, character-rich street near the lake. A harder search if you need a big yard, easy parking or plenty of listings, since landmark homes rarely come up for sale.
Get Personalized Guidance
LetsMovetoChicago.com founder John knows how to find the right real estate agent because he has been one since 2015. When it’s time to start your home search, John can connect you with a local real estate agent who specializes in the neighborhoods you’re focused on, at no cost to you!
Old Town Sign, Wells Street, Old Town, Chicago, IL
Crilly Court Rowhouses, Crilly Court, Old Town, Chicago, IL
Archway Standard Station (BP Gas Station), Clark Street and LaSalle Drive, Old Town, Chicago, IL
Wells Street, Old Town, Chicago, IL
Get the Old Town Neighborhood Report
Current selling trends, recent sale prices, commute times, and walkability.
What People Are Saying
Here's how people who live in Old Town describe it, summarized from public resident reviews:
⬇
Ready to see more of the Near North Side?
Check out the neighborhoods below.
