Located on the far south side of the city, Auburn Gresham is home to the Thurgood Marshall Branch of the Chicago Public Library and was the original location of the South Side Irish Parade. This neighborhood features historic bungalows and contemporary brick exteriors.

Sprawling across the western boundaries of the city, Austin is Chicago's most populous neighborhood yet still maintains a strong sense of community. The sheer size of the area, which spans from Garfield Park in the east to the edge of Oak Park in the west, makes it one of the most expansive in Chicago and home to a wide range of architecture, culture, and personality. The area’s landmark location, Austin Town Hall Park and Cultural Center, was once the town hall of the Village of Cicero, Illinois. Today, the space is used for park activities including a variety of dance, music and theater classes, music productions and more.

Avalon Park is known for its lush communal park and devoted, family-friendly residents. The small community is a cozy corner on the other side of the city’s noise. Marynook, for example, is a quiet suburban-inspired mini-community with architecture that hints at its post World War II roots.

Located on the city’s south side, Bridgeport is a popular neighborhood that offers a vibrant arts scene and is the birthplace of 5 Chicago politicians. Locals flock to the area to catch a Chicago White Sox game at Guaranteed Rate Field and experience the culturally inspired restaurants, bars, and family attractions.

Calumet Heights is a largely residential neighborhood located on the south side of Chicago. This is one area of the city where the vast majority of the homes are owner-occupied, which supports the fact that those who move here tend to stay. Per its name, the Calumet River is nearby, and even Lake Michigan is fairly close. The Pill Hill neighborhood is often considered part of Calumet Heights. This community is home to Bronzeville Children’s Museum. It is the first and only African American children's museum in the United States.

Chatham is a southside neighborhood straddling the busy Dan Ryan Expressway. Home to many employees of the city, it has a history of middle-class affluence, preoccupied with African-American families. As Chicago, and in particular, the south side, has evolved and changed throughout the past half a century, Chatham has been more consistent and remains as one of the most family-friendly neighborhoods in the area. The Chatham Market is a primary shopping destination for residents of the South Side which features big box stores, local retailers and eateries.

Stretching across Chicago's southeast landscape, Douglas is a well-established part of Chicago South Side. One of the city's most treasured beaches — 31st St Beach — sits along the neighborhood's eastern edge, while the abundance of green spaces make it a picturesque place to call home. Minutes from downtown but in the heart of one of the city's most dynamic neighborhoods, Douglas residents enjoy the attractions of city life while having a quaint, residential pocket to call their own.

East Garfield Park is a west side Chicago community where city life meets serenity. With its sister community, West Garfield Park, to the west, the neighborhood takes its name from the nearby Garfield Park, a Chicago Public Park that comprises 20% of this collective area. Situated near state-of-the-art hospitals and a world-class university, East Garfield Park is very much an up-and-coming area. Its main attraction is the Garfield Park Conservatory, one of the largest botanical conservatories in the United States.

A significant point on the map of southside Chicago, Englewood is one of the most historic and well-known Chicago neighborhoods. Once a site of busy shopping districts and a central intersection for railway systems, Englewood has undergone a significant transformation over the years and continues to be a focus of new renovation and revitalization projects. The neighborhood is a proud and historic one, having produced more than a few of Chicago's most celebrated children and sheltering several hidden gems within the city. Currently, Englewood has welcomed a shopping center that includes Whole Foods Market, providing healthier eating options for residents and students.

Logan Square is a bustling community of artists, popular nightlife, and home to disparate, diverse residents, from young professionals to indie creatives. A square surrounded by gothic mansions and single-family homes, this area is very popular. The centrally located park, where the neighborhood gets its name, is where all these diverse residents gather. Among the neighborhood are a variety of restaurants, hip coffee houses and boutiques. Built in 1918 to celebrate the 100th anniversary of Illinois' statehood, the Logan Square Monument is another attraction and landmark of Logan Square.

Sitting eight miles from the Loop, Grand Crossing is a neighborhood on the South Side of Chicago. It's part of Greater Grand Crossing, which includes other small pocket neighborhoods, like Parkway Gardens and Park Manor. Although the neighborhood still includes remnants of hard times, there exists a strong sense of community. Residents come together to clean up the city via a youth center. In addition, this neighborhood is home to a 2-unit brownstone where famed gangster Al Capone lived with his wife and mother.

This eclectic neighborhood is home to a unique culture that includes residents who have resided in Chicago for generations. Bordering the Stevenson Expressway, McKinley Park is located on the southwestern side of the city. Friendly residents and a beautiful park make this neighborhood a frequented spot for festivals and cultural events. The namesake park, McKinley Park, features a large lagoon, field house, swimming pool, tennis courts, athletic fields, as well as ice skating in winter months.

Named because it was near the former Union Stock Yards, Back of the Yards is a southwest side neighborhood that was home to European immigrants in the 20th century. Casual neighborhood bars and restaurants are plentiful in this area. For site-seeing, locals can check out Union Stock Yard Gate, the neighborhood’s National Historic Landmark located on Exchange Avenue.

South Chicago is a blue-collar neighborhood that was once known as a major steel manufacturing hub. While it no longer has the same strong ties to industrial labor, the community still maintains a working-class ethos in its small businesses and cozy restaurants. Where steel factories used to roar, vacant land by the lakefront awaits future developers to build in this area that has the potential for commercial and residential growth. Popular neighborhood parks and recreation include South Chicago Peoples Park and Jesse Owens Park, which features a newly constructed field house, a gymnasium, fitness center, and multi-purpose rooms.

Chicago’s South Loop is the biggest tourist destination because it is home to the Chicago Theater, The Field Museum, and Grant Park, which is popular for huge attendee summer festivals and events. The South Loop is a bustling community, offering breathtaking views of the city, an iconic theatre district, shopping, and fantastic eatery. The South Loop also houses Columbia College Chicago, a prominent media and arts school with notable alumni.

South Shore has been home to well-established and reputable Chicago businesses and professionals for several generations. This beachfront neighborhood offers stunning views and lush greenery and features some of the city's most diversified lakeside living options. A family-friendly neighborhood indeed, South Shore’s main attractions include Rainbow Beach, South Shore Cultural Center, and Stony Island Arts Bank.

Ukrainian Village is a historic community with a lot of charm, home to both the grit of urban life and the glamour of Michelin-rated establishments. The neighborhood is known for the restaurants, bars, and shops along its bustling sections of Chicago Avenue and Division Street. Further into the neighborhood exists single-family homes, brand new developments, and businesses that have been in the area for decades. Ukrainian Village retains much of the character of a European community. Tree-lined streets, small bungalows, as well as red-brick two-and three-flats, are the predominant architectural styles.

Located West of Hyde Park, Washington Park is an expansive residential neighborhood with a historic namesake park filled with small ponds, and lots of green lands. Surrounding the University of Chicago Hospital and Medical School, this neighborhood offers cozy restaurants that are frequented by students. Much like Bronzeville, Washington Park is known for its African American history, with the DuSable Museum being a landmark.

Railways and residences dominate the West Englewood community. Migrants originally relocated to this neighborhood for labor jobs in this industrial neighborhood. West Englewood is one of the city’s areas of focus for revitalization, and the classic 20th-century architecture makes each restored building look like a gem. In 2003, West Englewood became home to the West Englewood Public Library branch and is part of the Street Revitalization Project. It features a reading garden and environmentally sustainable construction.

Sitting in the shadow of the University of Chicago, Woodlawn is a unique locality offering culture, history, and housing just off the lakefront. University students and locals explore art galleries, ethnic food, and a walk through Jackson Park which provides some of the most picturesque views the city has to offer. Green Star Movement, a foundation dedicated to uplifting communities through public art, worked with youth from Woodlawn community groups plus hundreds of volunteers from throughout the city to transform the Woodlawn Gateway at 67th Street. The gateway mural incorporates musical imagery that reflects the community's jazz legacy as well as floral motifs that represent the Woodlawn Botanical Garden.