The Aquitania

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.

Chicago Lakeshore Hospital is a private behavioral health and addiction treatment center located in the north side of the city of Chicago, Illinois. In 2011 the hospital was cited for poor staffing, lax oversight, and numerous reports of sexual assault. Chicago Lakeshore Hospital opened its children's psychiatric center in 2013.In 2018, Federal authorities announced they were pulling funding from the hospital under investigation following numerous allegations of sexual abuse, assault and patient safety violations. All children in state care were removed from the facility after the ACLU of Illinois took action. Later that year, the facility's Medicare agreement was terminated.In 2020, the hospital closed temporarily, discharging its final patient after years of scrutiny. The Covid 19 pandemic was cited as the reason for the facility’s closure.

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 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.

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.

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.

Argyle is a station on the Chicago Transit Authority's 'L' system. It is situated between the Berwyn and Lawrence stations on the Red Line, which runs from Rogers Park at Chicago's northern city limits, through downtown Chicago, to Roseland. It is an elevated station with an island platform serving northbound trains and a temporary side platform serving southbound trains located at 1118 West Argyle Street in the West Argyle Street Historic District of Chicago's Uptown community area. Purple Line weekday rush hour express service use the outside tracks but do not stop at this station.

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.

Park Tower Condominium is a lakefront high-rise residential building located at 5415 North Sheridan Road, in the Edgewater neighborhood of Chicago. Constructed in 1973, the tower is 55 stories tall total and 513 feet (156 m) high (the 2nd tallest structure outside of downtown Chicago). It is one of the largest all-residential buildings in Chicago. Designed by Chicago architectural firm Solomon, Cordwell, Buenz and Associates, the building was originally planned to be part of a 3-tower complex. The building was originally constructed as rental apartments, but was converted to condominiums in 1979.

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

The W. C. Reebie and Brother Building is a building on Broadway in Chicago's Uptown community, and is a contributing property to the West Argyle Street Historic District.

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.