St. Michael's Church, Old Town, Chicago

Old Town is a neighborhood and historic district in Near North Side and Lincoln Park, Chicago, Illinois, home to many of Chicago's older, Victorian-era buildings, including St. Michael's Church, one of seven buildings to survive the Great Chicago Fire.

Sedgwick is an 'L' station on the CTA's Brown Line, Purple Line Express trains also stop at the station during weekday rush hours. It is an elevated station with two side platforms, located in Chicago's Old Town neighborhood of the Near North Side community area. The adjacent stations are Armitage, which is located about one mile (1.6 km) to the northwest, and Chicago, located about one mile (1.6 km) to the south.

The Henry Gerber House is located on North Crilly Court in the Old Town neighborhood of Chicago, Illinois, United States. It is a single-family brick row house built in 1885 in the Queen Anne style, mostly intact from that time. In the 1920s it housed the apartment occupied by German-born Henry Gerber, founder of the short-lived Society for Human Rights, which was incorporated in Illinois as the first American organization working for gay rights. Inspired by nascent gay-rights organizations he had seen in Germany, Gerber held meetings here and published newsletters, the first known gay civil rights periodicals in the country, for a year until the Chicago police raided the house in 1925. The Gerber House was recognized as a contributing property to the Old Town Triangle Chicago Landmark District when that was established by the city in 1977, and then when it was listed as a historic district on the National Register of Historic Places in 1984. The building was designated a Chicago Landmark in 2001. In June 2015 it was named a National Historic Landmark.

Larrabee, also known as Larrabee & Ogden, was a station on the Chicago Transit Authority's North Side Main Line, which is now part of the Brown Line. The station was located at 1540 N. Larrabee Street in the Near North Side neighborhood of Chicago. Larrabee was situated east of Halsted, which closed at the same time as Larrabee, and north of Sedgwick. Larrabee opened on June 6, 1900, and closed on August 1, 1949, along with 22 other stations as part of a CTA service revision.

The Marshall Field Garden Apartments is a large non-governmental subsidized housing project in the Old Town neighborhood of Chicago, Illinois. The project occupies two square city blocks and was the largest moderate-income housing development in the U.S. at the time of construction in 1929. Marshall Field Garden Apartments has 628 units within 10 buildings. Polo G lived in the project in his youth.

The Old Town Ale House is a saloon in the Old Town neighborhood of Chicago, United States, that has been operation since 1958. It is currently located at 219 W. North Avenue.

The Second City is an improvisational comedy enterprise. It is the oldest improvisational theater troupe to be continuously based in Chicago, with training programs and live theaters in Toronto and New York. Since its debut in 1959, it has become one of the most influential and renowned in the English-speaking world. In February 2021, ZMC, a private equity investment firm based in Manhattan, purchased the Second City. The Second City has produced television programs in both Canada and the United States, including SCTV, Second City Presents, and Next Comedy Legend. It has been a starting point for many comedians, award-winning actors, directors, and others in show business, including Del Close, Alan Alda, Alan Arkin, Harold Ramis, Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Eugene Levy, Catherine O'Hara, Dave Thomas, Chris Farley, Tim Meadows, Colin Mochrie, Ryan Stiles, Mike Myers, Nia Vardalos, Steve Carell, Jordan Peele, Tina Fey, Amy Poehler, Stephen Colbert, Cecily Strong, Mae Martin, and Aidy Bryant.

The Carl Street Studios is an enclave in Chicago's Old Town neighborhood.

Zanies Comedy Club, located in Chicago, Illinois, was founded in November 1978 by Rick Uchwat. Since then, three other locations have been built: Nashville, Tennessee, St.Charles, Illinois, and Rosemont, Illinois.

Schiller was a station on the Chicago Transit Authority's North Side Main Line, which is now part of the Brown Line. The station was located at 315 W. Schiller Street in the Near North Side neighborhood of Chicago. Schiller was situated south of Sedgwick and north of Division, which closed at the same time as Schiller. Schiller opened on May 31, 1900, and closed on August 1, 1949, along with 22 other stations as part of a CTA service revision.

Near North Career Metropolitan High School (formerly known as Near North Career Magnet High School and Near North Career Academy High School) was a public 4–year magnet high school located in the Old Town neighborhood on the Near North Side of Chicago, Illinois, United States. Operated by the Chicago Public Schools district, Near North opened in September 1979. Near North served as a new and replacement school for the area when Cooley Vocational High School was closed at the end of the 1978–1979 school year due to inadequate conditions within the building. In addition to being a magnet school, Near North offered vocational courses through the Education To Careers (ETC) program. Near North closed in June 2001 due to the decline in its enrollment and the city's plans for the surrounding neighborhood.

A Red Orchid Theatre is an Equity theatre company located in the Old Town district of Chicago, founded in 1993 by Michael Shannon, Guy Van Swearingen IV, and Lawrence Grimm. Kirsten Fitzgerald, a long-time ensemble member, has helmed the company as Artistic Director since 2008.