Slot Machines for Bars in Old Town, Chicago

History

German immigrants settled the Old Town Triangle in the 1850s, and their community life centered on St. Michael's Church, the City's landmark record says. The Fire of 1871 destroyed all of the houses and most of the church. Small frame workers' cottages went up again until a city ordinance banned more wood construction, and larger brick and stone houses followed. In 1948 residents worried about physical decline formed the Old Town Triangle Association, the Encyclopedia of Chicago says, and the name Old Town stuck. The City made the Triangle a Chicago Landmark district in 1977.

The Old Town School of Folk Music opened in December 1957 with its first home on North Avenue, and The Second City opened in December 1959. The Encyclopedia says residents relished having both in the 1960s. Wells Street, the commercial strip through the neighborhood, drew a boom in fashionable restaurants and stores, and residents resented the noise, trash and crowds. Late in the decade it became a hippie gathering place, and some new shops failed.

The area today

The landmark district is bounded by Lincoln, North, Wells and the former Ogden right-of-way, and the City credits a 1940s revival with preserving its narrow tree-lined streets. The Old Town Merchants & Residents Association, founded in 1971, centers its work on the Wells Street commercial corridor, which it describes as home to retailers, bars and restaurants, comedy clubs and independent theater. It names The Second City and St. Michael's Church among the neighborhood's attractions.

The association points festival visitors to the Brown Line's Sedgwick stop. CTA lists that elevated station at 1536 N. Sedgwick St., with the 37 and 72 buses half a block north. The association's Wells Street Art Festival, on Wells from North Avenue to Division Street, ran June 13 and 14, 2026, and its Old Town Oktoberfest, which celebrates the neighborhood's German heritage, returned to Wells between Schiller and Evergreen in September.

Bars and restaurants here

The merchants' association says Old Town's multigenerational businesses include historical bars. Special Service Area 48 provides on-street security patrols focused on weekend evenings from mid-March until New Year's Eve. In October 2023 the City Council approved a liquor moratorium on Wells from Schiller Street to North Avenue, with current license holders grandfathered in. FOX 32 reported in December 2024 that a Wells Street bar was ending a 13-year run at its site.