Chicago Lakeshore Hospital

Castlewood Terrace is a block-long street and residential historic district in the Uptown neighborhood of Chicago, Illinois. The district includes 26 single-family houses built between 1897 and 1927. The street is highly unusual compared to its surroundings, as both Uptown and Chicago's lakeshore in general were built up with high-rise apartments in the early twentieth century; Castlewood Terrace residents resisted high-rise construction for decades after the street's development. Most of the houses are two to three story brick structures with spacious lots and front driveways, giving the street visual consistency despite the many different architectural styles used in its homes. Some of these architectural styles include Tudor Revival, Renaissance Revival, Foursquare, Colonial Revival, and Queen Anne.The district was added to the National Register of Historic Places on September 3, 2009.

The Aquitania is a luxury, 82-unit cooperative apartment building in the Margate Park neighborhood of the Uptown community of Chicago, Illinois. It is officially designated on the National Register of Historic Places by The United States Department of the Interior. The Aquitania, known legally as the 5000 North Marine Drive Corporation, was built by Ralph C. Harris and Byron H. Jillson in the Classical Revival style. Its developer was George K. Spoor, the co-founder of Essanay Studios and a producer of silent movies during the first two decades of the 20th century. At that time, Chicago rivaled both New York City and Hollywood in film production, and Spoor was able to use his considerable wealth to plan and develop a property, which he felt was befitting the celebrities connected with Chicago's growing entertainment industry. A legend, which purports that Essanay Studio actors Charlie Chaplin and Gloria Swanson once resided at The Aquitania, is likely unfounded. This probable factual inaccuracy reflects nothing more than film lore since all silent film production left Chicago's Essanay studios for southern California by 1918 at the very latest, and The Aquitania was not built until 1923, although there are historical accounts of both silent-film era stars staying as guests at The Aquitania when it was a hotel in its earliest days. When the Aquitania was built, it was situated directly on the Lake Michigan shore; subsequent development of both Lake Shore Drive and the lakefront park have moved the shore some two blocks east of the building. The fifteen-story building has a courtyard and an Art Moderne lobby. Construction was completed in 1923, and it became a cooperative in 1949.

Louis A. Weiss Memorial Hospital, is an urban hospital located in the Uptown neighborhood of Chicago, Illinois. It is a 236-bed hospital, located on the site of what used to be Clarendon Beach, a popular beach of the city. Until the 2000s, Weiss Hospital had been part of the University of Chicago Hospitals system.Beginning in July 2012, Weiss Memorial Hospital joined the other four Tenet Healthcare hospitals in Chicago as an Accountable care organization, part of the Center for Medicare and Medicaid's Shared Savings Program.In January 2019, Tenet Healthcare sold its three remaining Chicago-area for-profit hospitals to Los Angeles-based Pipeline Health, which is partially owned and operated by Dr. Eric E. Whitaker, a friend of former United States president Barack Obama. The three hospitals in the sale are Louis A. Weiss Memorial Hospital, Chicago, Illinois; Westlake Hospital, Melrose Park, Illinois; and West Suburban Medical Center, Oak Park, Illinois.

The Preston Bradley Center is a nationally registered historic building in Chicago, Illinois, U.S.A. Its creators designed the site as a center for arts and culture. The building was constructed in 1925, and designed by British-American architect J.E.O. Pridmore. In 2000 the building was placed on the Federal Register of Historic Places by the United States Department of the Interior. In 2015, the City of Chicago began the process of designating the Preston Bradley Center as a historic landmark. It is named after Preston Bradley, a pastor in Chicago. The landmark was occupied by Peoples Church in 1926, then sold to the Chicago orthopedist Daniel Ivankovich in 2022. Two of the building’s most important interior rooms are the auditorium, which has two balconies, and a mural by Chicago artist Louis Grell; and Mason Hall, adorned with artwork suggesting Bradley’s ties to the masons.

Eastwood By The Lake, formerly known as Eastwood Beach Apartment Hotel, is a condominium and apartment building in the Uptown neighborhood of Chicago. It is the oldest known Residential Hotel built in Chicago during the twentieth century. It was designed in 1912 by distinguished Architect John Augustus Nyden as a glamorous unique hotel with 25 balconies, lounging room and a rooftop ballroom next to the beach. It was renovated in the 2000s and is located across the street from the Louis A. Weiss Memorial Hospital.

Big Chicks is a gay bar and neighborhood restaurant that opened in 1986 in Uptown, Chicago. It serves a diverse group of LGBT people, straight people and people in the kink community. The owner of the establishment is Michelle Fire. The restaurant next door, Tweet, is also owned by Fire and provides food to Big Chicks.

The Sheridan Plaza Hotel is a historic hotel located at the corner of Wilson Avenue and Sheridan Road in the Uptown neighborhood of Chicago, Illinois.

The Uptown Square Historic District is a commercial historic district encompassing parts of Broadway and Lawrence Avenue in the Uptown neighborhood of Chicago, Illinois. Primarily developed between 1900 and 1930, the district was Chicago's largest commercial and entertainment hub away from downtown in the early twentieth century. The opening of Wilson station on the Northwestern Elevated Railroad spurred the area's development, as the transit line made Uptown's beaches an accessible tourist destination for the rest of the city. Many stores, restaurants, theaters, and clubs sprang up to cater to the area's new tourists, and it soon became a destination for young, single Chicagoans seeking entertainment. The district includes several prominent entertainment venues, including the Balaban and Katz-run Uptown Theatre and Riviera Theatre, the Aragon Ballroom, and the Green Mill nightclub.The district was added to the National Register of Historic Places on November 8, 2000.

The West Argyle Street Historic District (also known as "Little Saigon", "New Chinatown", "Argyle Square", "Asia on Argyle", or "Argyle Park") is a historic district in the northern Uptown, a commercial district of Chicago, Illinois. It was listed on the National Register of Historic Places on June 3, 2010. The community covers an area of about 41 acres (0.17 km2); its rough boundaries are N. Glenwood Ave to the west, Winona Street to the north, Sheridan Road to the east, and Ainslie Street to the south. It was home to the Essenay Studios in the 1920s founded by Charlie Chaplin, a producer of silent movies before relocating to Southern California in Hollywood. Essenay Studios now is home to St. Augustine College.

The Aragon Ballroom is a ballroom located in Chicago, Illinois, approximately 5 miles (8 km) north of downtown, in the Uptown neighborhood.

Lawrence is a temporarily closed 'L' station on the Chicago Transit Authority's Red Line. It is an elevated station located at 1117 West Lawrence Avenue in the Uptown neighborhood of Chicago, Illinois. The adjacent stations are Argyle, located about 1⁄3 mile (0.54 km) to the north, and Wilson, about 1⁄4 mile (0.40 km) to the south, serving as alternate stations remaining open while Lawrence is closed for reconstruction. Four tracks pass through the station, though the two eastern tracks are out of service for reconstruction, with a single island platform in the center of the tracks; Purple Line weekday rush hour express service use the outside tracks and do not stop. Lawrence station is located in the historic Uptown entertainment district. Nearby attractions include the Aragon Ballroom, the Green Mill Cocktail Lounge, the Riviera Theater, and the Uptown Theatre.

The Uptown Broadway Building is a historic three-story building at 4703–4715 North Broadway in Uptown, Chicago. Built in 1926, it was designed by Walter W. Ahlschlager and is known for its ornate terra-cotta facade, depicting ancient gods, rams' heads, shields, helmets, birds, fruits, and trophies. Lynn Becker of the Chicago Reader has called the exterior "a riotous, Spanish-baroque-inspired hallucination". According to unconfirmed local legends, Al Capone operated a speakeasy in the building's basement.The building was listed on the National Register of Historic Places in 1986. It is also listed as part of the Uptown Square Historic District.On December 31, 2013, the Kiss Kiss Cabaret announced they have chosen it for their new location.