Living in Old Town: Wells Street, History, and Daily Life

How walkable is Old Town?

Old Town is highly walkable, meaning most daily errands can be completed on foot rather than by car. The neighborhood's compact blocks, ground-floor retail, and short distances to dining and transit support a pedestrian-oriented routine. As of June 2026, an Old Town address carries a Walk Score of 97 ("Walker's Paradise"), a Transit Score of 86 ("Excellent Transit"), and a Bike Score of 93 ("Biker's Paradise"), per Walk Score. The same scoring notes that daily errands in the area do not require a car.

Walkability is shaped by the corridor itself. Wells Street concentrates restaurants, cafes, and independent shops, while the side streets of the Old Town Triangle stay residential and quiet. The lakefront, Lincoln Park, and the CTA station at Sedgwick are all within a short walk, which is part of why the neighborhood reads as a connected, on-foot place rather than a drive-everywhere one.

Mobility measure	Old Town address	Label
Walk Score	97	Walker's Paradise
Transit Score	86	Excellent Transit
Bike Score	93	Biker's Paradise

Scores reflect a single representative Old Town address as reported by Walk Score in June 2026 and may vary block to block. For a fuller orientation, see the Old Town neighborhood guide.

What is the commute like?

The commute from Old Town leans on the CTA, meaning rail and bus access put downtown and the wider North Side within reach without driving. The neighborhood's primary rail stop is Sedgwick station, at 1536 North Sedgwick Street in the 60610 ZIP code, which is served by the Brown Line and by the Purple Line Express during weekday rush hours, per Wikipedia. That same source reports Sedgwick recorded approximately 852,239 boardings in 2025, an increase of about 4.3% over the prior year.

From Sedgwick, the Brown Line loops through the Loop business district, while bus routes along Wells Street, Division, and North Avenue add coverage for trips the rail lines do not serve directly. The CTA publishes current schedules and service details through the Chicago Transit Authority. Cyclists also benefit from the area's connectivity, with the Lakefront Trail a short ride east toward Lake Michigan. Choose Chicago offers a broader overview of getting around the city, available via Choose Chicago.

What is the Old Town Triangle and its history?

The Old Town Triangle is a historic district at the heart of the neighborhood, meaning a designated, protected area whose streets and architecture are preserved. The Old Town Triangle Historic District was designated a Chicago Landmark on September 28, 1977, and added to the National Register of Historic Places on November 8, 1984, per Wikipedia. Many of its streets and alleys predate the Great Chicago Fire of 1871 and depart from Chicago's standard grid, which is why the area's cobblestone lanes and Victorian-era rowhouses feel distinct.

St. Michael's Church anchors the district and is one of only seven buildings within the city limits known to have survived the Great Chicago Fire, according to Wikipedia. Local lore held that anyone living within hearing distance of the church bells was an "Old Towner." The Moody Church sits nearby at the neighborhood's southern edge, adding to the area's collection of historic religious architecture.

The Old Town Art Fair grew out of this same community. First organized as the "Old Town Holiday" in June 1950 to raise funds for a local club, it now draws more than 200 artists to the Triangle each June, per Wikipedia. The 2026 fair was held June 13 and 14 within the Triangle Historic District, according to the Old Town Art Fair.

Where do people eat, shop, and go out on Wells Street?

Wells Street is Old Town's main commercial corridor, meaning the spine where dining, shopping, and nightlife concentrate. The street mixes restaurants, cafes, bars, and independent boutiques with cultural venues, so a single walk can cover everyday errands and an evening out. Its best-known institutions are tied to Chicago's comedy history.

The Second City, the improvisational theater founded in 1959, is central to that identity. Its first revue premiered on December 16, 1959, at 1842 North Wells Street, and the company moved a few blocks south to 1616 North Wells in 1967, where it has remained, per Wikipedia. Nearby, the iO Theater contributes to the area's long-running improv scene. Beyond the theaters, the corridor supports neighborhood staples and the seasonal Sedgwick farmers market, while Lincoln Park and the lakefront provide green space a short walk away. Choose Chicago maintains current listings for Old Town dining and attractions through Choose Chicago.

For residents weighing a move, the corridor's blend of culture and convenience is often a deciding factor. Those exploring next steps can review buying a home in Old Town or selling a home in Old Town.

What should families know about schools?

Households researching schools in Old Town typically look at both Chicago Public Schools options and the area's independent schools, meaning attendance boundaries and enrollment policies vary by address and program. Because catchment areas shift, the most reliable approach is to confirm a specific home's assigned schools rather than rely on neighborhood generalizations.

Independent ratings and enrollment details for nearby public and private schools are published by GreatSchools, available through GreatSchools, and official boundary and program information comes directly from Chicago Public Schools. Old Town's central position on the Near North Side also places it within reach of the cultural and recreational resources of Lincoln Park, which many households factor into daily routines alongside formal schooling. For a complete picture of the neighborhood, the Old Town neighborhood guide connects these threads together.