When visiting Old Town on Chicago’s north side, you will be greeted by its iconic scrolling entryways, a fittingly regal welcome for this Windy City neighborhood, which boasts one of the city’s largest concentrations of Victorian-era buildings. Old Town offers a mix of quaint charm and modern culture, while the pedestrian-friendly streets—many still laid out according to a pre-Great Chicago Fire map—host a bustling commercial center with some of the city’s trendiest restaurants, theaters, pubs, and boutiques. From shops with specialty olive oils to a gastropub with over 90 brews on tap, and from Second City to antique Bavarian churches, Old Town is the Windy City’s version of what happens when tradition merges with urban chic.
A wave of German immigrants defined Old Town's early days, transforming it from the swampy farmland that characterized the area during the late 19th century. Their influence can still be felt in the neighborhood's Victorian-era structures, a number of which survived the Great Chicago Fire, including the Bavarian-styled St. Michael's Church. Also linking Old Town to its early roots is the Old Town Triangle District, which predates Chicago's later grid-style street pattern. As Old Town developed in the 1960s, the area became a center for Midwestern hippie culture, championing LGBT rights and becoming a hub for Chicago folk music.
From Old Town's early German Catholic settlers to the progressive counterculture of the 1960s, today's neighborhood appeals to anyone interested in Chicago history and modernity. Old Town's refurbished historic section provides a contrast to areas still awaiting economic development, while newer Chicago institutions like Second City bring the neighborhood squarely into the forefront of American culture. From college students auditioning at established theaters to professionals who appreciate the neighborhood's proximity to the Loop, Old Town is a perfect spot for newcomers, families, and long-time Chicagoans alike.
Old Town overflows with landmarks, from Chicago's famed improv comedy troupe Second City to the city's lauded Steppenwolf Theatre. Rounding out the arts culture is the Old Town Arts Fair, featuring over 250 artists outdoors in the historic district every summer. For those itching to learn more about the area's history, Old Town offers the new Chicago History Museum. And, even though Chicago's beloved Old Town School of Music has since moved neighborhoods, it's doubtful anyone in Old Town can forget where it all began.