Old Town Ale House, Chicago

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.

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.

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.

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.

The Carling Hotel is a historic residential hotel located at 1512 N. LaSalle Street in the Near North Side neighborhood of Chicago, Illinois. Built in 1927, the hotel was one of many residential hotels constructed to house an influx of labor to Chicago in the early 20th century. While the hotel offered rooms to both temporary and permanent residents, census records indicate that most of its residents were permanent. Architect Edmund J. Meles, who designed several large hotels and apartment buildings in Chicago, designed the building in a blend of the Classical Revival and Renaissance Revival styles. The brick building features extensive terra cotta ornamentation, including entrance and window surrounds, pilasters, and a molded cornice above the first floor.The building was added to the National Register of Historic Places on January 24, 2017.

The West Burton Place Historic District is a residential historic district located at 143-161 W. Burton Place in the Near North Side neighborhood of Chicago, Illinois. The district, which includes twelve main houses and five carriage houses, was developed in the late 19th century but renovated into an artists' colony in the 1920s and 1930s. Artist Edgar Miller and businessman Sol Kogen began the district's redevelopment by redesigning and opening Carl Street Studios in 1927; at the time, Burton Place was known as Carl Street. Kogen and Miller, as well as other Chicago artists, gradually converted other homes on the street into artists' studios and residences. While the homes started off as Italianate or Queen Anne structures that had become dilapidated by the 1930s, their redesigns featured then-modern styles such as Art Deco and Art Moderne; five of the street's homes retain their original designs, providing architectural contrast. The district was added to the National Register of Historic Places on December 6, 2007. The cul-de-sac was later designated a Historic District by the City of Chicago after one of the buildings was threatened by demolition. The landmarking effort was led by author Keith Stolte, attorney and Chicago Art Deco Society Vice President Amy Keller, and Edgar Miller Legacy founder and Executive Director Zac Bleicher.

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

The Germania Club Building, located at 108 W. Germania Place in the Near North Side community area of Chicago, Illinois, is the historic headquarters of the Germania Club, the oldest German-American organization in the city. The Germania Club was founded in 1865 as the Germania Männerchor, which formed to sing at Abraham Lincoln's funeral. The club built the Germania Club Building in 1889; it was designed by August Fiedler in an eclectic style featuring neoclassical and German Renaissance influences. The five-story building has a two-story limestone base with a portico and arched doorway on the south end. The upper stories feature arched windows capped by pediments and a pilaster supporting the cornice atop the building. The building includes a grand ballroom, banquet room, and restaurant and bar. The club played an important role in Chicago's German-American community, once the largest ethnic community in Chicago.

The Moody Church (often referred to as Moody Memorial Church, after a sign hung on the North Avenue side of the building) is a historic evangelical Christian (Nondenominational Christianity) church in the Lincoln Park neighborhood of Chicago, Illinois.

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.

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.

A statue of René-Robert Cavelier, Sieur de La Salle (sometimes called Robert Cavelier de LaSalle Monument) is installed in Chicago's Lincoln Park, in the U.S. state of Illinois. The work by Count Jacques de la Laing was completed in 1889 and relocated in 1990.