Once an elegant, Victorian-style suburb on Chicago's south side, Oakland neighborhood is making a strong comeback to reclaim its status as a prominent and flourishing community. Today, many of Oakland's quiet residential streets are sprouting manicured lawns with newly built single-family homes and multi-unit constructions. Full-on neighborhood revitalization is spearheaded by enthusiastic local organizations and community centers that have set up educational and recreational programs for Oakland residents of all ages and interests. Sports teams, exercise classes, head start pre-school curriculums, financial workshops, computer courses and networking events are all available to the public.

Oakland Facts

Location: About 5 miles southwest of the Loop
Boundaries: 35th Street to the north, Lake Michigan to the east, 43rd Street to the south, and Drexel Boulevard and Cottage Grove Avenue to the west
Bordering Neighborhoods: Bronzeville, Douglas, Kenwood

Then and Now

Oakland Real Estate

The Oakland neighborhood area is a mile-long strip hugging Chicago’s southern lakefront. This former swamp area was the original site for one of the city’s first soap and lard rendering factories owned by an Englishman named Charles Cleaver. Cleaver played an important role in establishing the neighborhood when, in 1851, he began building wooden homes, in addition to a general store, a place to worship, and a town hall for his employees between 37th and 39th streets. During this time the settlement was known as 'Cleaverville,' but within a couple decades the newly constructed Illinois Central Railroad boosted development in the area and it was renamed Oakland in 1871.

By the 1880s, the easily accessible cable cars and trains to downtown attracted many well-to-do businessmen and their families to Oakland. Mass production of single-family homes reached its peak by 1895, and no sooner had this south side Chicago neighborhood established a prestigious name for itself did it quickly return to its workers’ town roots. Wealthy residents left the area and working class Irish stockyard families moved in during the early part of the 20th century.

During the 1930s, new construction and economic growth were at a standstill. But ten years later, things began to change. Oakland’s population soared from 16,000 to 24,000 residents between 1940 and 1950—the majority of which were African American families, with a smaller community of displaced Japanese Americans who were forced to relocate because of a WW II policy. Through the 1950s, to better cope with the spike in population, the Chicago Housing Authority constructed a 150-unit building called the Victor Olander Homes at 39th Street and Lake Park Avenue. Several other large housing projects soon followed. In 2007, only half of these low-income housing developments remain.

Today, Oakland is boldly and steadily making its way out of hardship and deterioration. The neighborhood has witnessed rejuvenation in certain pockets with new construction and refurbishing of older buildings, but there’s still a long road ahead before it is revitalized to its mid 19th century glory.


The love of tradition, nature and recreation endures at Oakland’s charming Mandrake Park, situated in the center of the neighborhood.

Mandrake Park (900 E. Pershing Rd., 312-747-7661) was a joint venture between the Chicago Department of Transportation and the Chicago Park District. They worked cooperatively with the aid of local residents to bring nearby Douglas neighborhood inhabitants and Grand Boulevard residents together as one community with the construction of a new park. In 1998, plans for a multi-purpose athletic field, a running track, and a landscaped border to buffer the park from traffic, was launched.

This park was named after Henry McNeil 'Mandrake' Brown, a social activist who initiated grassroots efforts to ban alcohol and tobacco related billboards in Chicago residential neighborhoods, especially where schools and churches were located. He was successful in the removal of 700 illegal billboards throughout Chicago.

Okay, enough of the local history lesson—let’s talk about what programming and facilities Mandrake Park offers us. 'Movies in the Park' is a perfect family outing during the warm summer months. Just grab a blanket, a couple of lawn chairs, some microwaved popcorn, and your loved ones and join the local moviegoers on the grass. The films are suitable for all ages and admission is always free. For a dose of recreational softball, spend some time with new and old friends out on the diamond, or if softball’s not your game, tennis is another ace that’s served up at this south side Chicago neighborhood park. And don’t forget, Mandrake Park is about 8 blocks west of the lakefront where you’ll encounter a number of walking and bike trails off of Oakwood Avenue.

Oakland Real Estate

Much of the beauty in Oakland neighborhood is its unique melange of architectural masterpieces. Take a stroll down any number of streets and you’ll be sure to encounter new developments as well as rehabbed condominiums and stately, century-old single-family homes.

In the late 19th century, Oakland neighborhood was one of the exclusive A-List members of the upper-class Victorian mansion communities of Chicago. Some of the houses that survive from that golden era include cottages designed in the Queen Anne style, as well as some impressive Romanesque and Classical Revival homes that were designed by prominent architects. The architectural styles that distinguish the community, though, are the Queen Ann residences that are generally simple, yet elegant in ornamentation with large porches and multiple chimneys. Classical Revival architecture was one of the most popular styles in the United States during the late 1800s and early 1900s. This contemporary interpretation of ancient Greek and Roman engineering can be found throughout Oakland, particularly in the churches and public buildings. Some common characteristics of this school are columns, symmetrical facades, and the edifices are generally made of stone, brick, or wood.

And finally, the Romanesque school made its presence in Oakland with medieval inspired French and Spanish architecture. In the 1880s, architect H. H. Richardson had a hand in putting his signature style on projects that include private homes, clubs, and commercial buildings scattered throughout the community. The common characteristics are heavy rough-cut stonewalls, round arches and squat columns, and deeply recessed windows. In the last few years, developers have reclaimed many of these classic structures and they are in the process of becoming luxury condominium conversions.

In 2000, the Chicago Housing Authority, partnered with non-profit and private developers, launched an ambitious plan to do away with its decaying high-rise projects from the 1950s. They successfully replaced the rundown buildings with mixed-income housing for sale or lease at affordable market rates. And, in the near future, the City of Chicago plans to construct an architecturally significant pedestrian bridge linking the new residential developments to Burnham Park, along the waterfront. Many of the condos located along the lamppost-lined redeveloped streets east of Langley Avenue boast detailed workmanship and high-end amenities. Luxurious units with heated marble floors and oversized Jacuzzi tubs make for a peaceful urban existence.

The average sales price for a two-bedroom condo in Oakland neighborhood is around $260,000. For a three-bedroom unit the average price jumps up to about $335,000. A three-bedroom detached single-family home ranges between the mid $200,000s and the mid $500,000s with the average sales price around $430,000. For a place with another bedroom or two, the range stretches a bit—with some of the larger new construction and renovated older homes valued at over a million dollars.

Community that Cares

Improve the quality of your family’s life at Abraham Lincoln Centre where you’ll have access to programs for your pre-school aged child as well as activities for yourself and your parents in their golden years. Abraham Lincoln Centre (3858 S. Cottage Grove, 773.285.1390) was established in 1905 by the All Souls Church to increase social, intellectual and cultural activities for community members. This south side Chicago center focuses on educational, recreational and self-improvement programs for Oakland residents as well as members of the surrounding communities. The rapidly changing neighborhood, due to gentrification and re-development, has the Centre expanding its programs to better suit the needs of an emerging new community identity.

The Centre’s all boy wrestling team, the 'Scramblers,' are always up for a competitive season, especially when they’ve had the luxury of training with Olympic Gold Medalist and world champions greats like Ben Peterson, Dan Gable and John Peterson. Other exciting sports activities include 10-week basics in judo—offered to both children and adults—it makes for a wonderful family activity.

For the little ones in the home, consider The Head Start and Early Head Start programs at the Abe Lincoln Centre. It is a bright and friendly place for children who are at the brink of starting school. The programs are designed for kids 3 to 5 years of age where the teachers instill a love and desire for learning and having fun. If you are new to the area the Adult & Senior Services Division is a helpful resource center for adults of all ages to find new employment opportunities as well as workshops on financial planning. If you’re in need of brushing up your computer skills, the Centre offers technology training too. We can all appreciate the benefits of networking, particularly for those of us that are new to a community or city!

Kenwood Oakland Community Organization (KOCO) (1005 E. 43rd St. 773.548.7500) is another life enriching foundation that the entire neighborhood can take part in. KOCO offers 40 years experience in social and political empowerment programming. Whether we want to actively participate in community affairs or we just need a place to register to vote—KOCO provides these services and more.

What’s on the Menu?

Oakland is predominantly residential and the selection of places to eat out is minimal except for a few carry-out institutions.

For a classic Chicago Italian beef sandwich, bathed in seasoned gravy, there’s no better place to go in Oakland neighborhood than Tastee Beef (4248 S. Cottage Grove Ave, 773-373-7089). Sink your teeth in and you’ll be in heaven. They’ve also got an expansive fish fry menu in addition to gyros, tacos, hot dogs, subs, popcorn shrimp and burgers. And once you’ve tried Tastee’s tasty comfort food, there’s no doubt you’ll find yourself back again for another dose of this south side neighborhood specialty. Everything is 'to go' and service is lightening fast, so it’s a handy stop for a quick lunch break. Sadly, there is no delivery service.

Another neighborhood joint dedicated to fish fry of all kinds is Shark’s (4048 S Cottage Grove Ave, 773-538-4889). Their menu looks like a 'catch of the day' list with catfish, Lake Superior white fish, Jack salmon, shrimp, and the not-so-fish-like fried chicken. We like the convenience of eating our catch on sight under the warm fluorescent lights and shabby chic dining area, especially after a late night out on the town—Shark’s is open from 10am until the wee hours everyday except Sunday.

Best Shopping Stops

Sometimes paradise is just beyond your own backyard. For Oakland residents, surrounding yourself in soothing beauty and relaxing tranquility is easy with two of life’s simplest pleasures found right here in this south side neighborhood.

Considered a south side institution, New Age Chicago (4238 S Cottage Grove Ave, 773-285-3765) is a family-owned and operated home furnishings retail store and warehouse that has been around for 80 years. Phillip Kaplan is the third generation of Kaplans to run the family business and its 7,500 square feet of living room, bedroom, and kitchen furniture. New Age also sells plasma televisions, audio and video/DVD equipment, and entertainment centers—to keep all those gadgets and electronics well organized. Go ahead, pamper your home with all the conveniences of modern living. Repeat second and third generation customers will tell you—they love the contemporary style of the merchandise at New Age, as well as their affordable prices.

Where there’s a will there’s no better way to escape the daily grind than a rejuvenating spa treatment. Soul Salon (4256 S Cottage Grove Ave, 773-268-3390) offers its clients full-service hair care, manicures, spa pedicures, brow arch, and even makeup and fashion consulting. The tension will melt away as you recline in the massage chair and feel the bubbling whirlpool tickling your toes in the foot Jacuzzi. Sip on a freshly made smoothie from the juice bar while relaxing under the touch of professional beauty specialists—give them one hour, and you’ll leave Soul Salon a whole new person.

Getting Around

Fortunately, Chicago has one of the best public transportation systems in the nation and every neighborhood, including Oakland, has either a train station or bus service just a few blocks from your door.

Oakland neighborhood’s grand boulevards and residential streets offer ample free parking for yourself, friends and family, in addition to secure gated parking for your special ride. If you are traveling by car, access to Lake Shore Drive from Oakland is a few stoplights away at Oakwood Avenue where you can easily connect to I-55 (Stevenson Expressway), I-90/94 (Dan Ryan Expressway) and I-290 (Eisenhower Expressway) in a matter of minutes.

Commuters who prefer to use public transportation can catch the Chicago Transit Authority (CTA) Green Line train at 40th Street and Indiana Avenue—a healthy seven block walk west from the fringes of the Oakland neighborhood. Passengers can take the Green Line right into the Loop, and if you continue to ride, it will take you to the Garfield Conservatory and out to Oak Park suburb. Another convenient alternative to the 'El' (so-named because it’s an elevated public transit train; also part of the subway system) is the Metra Electric Line (Chicago’s main commuter train system to and from the suburbs). The closest station for Oakland residents is at 47th Street near Lake Park Avenue, which drops you right into Millennium Station, formerly known as the Randolph Street Station on Michigan Avenue between Water and Randolph streets.

Over a dozen CTA bus lines are also easily accessible in Oakland neighborhood, giving residents another travel option that we think is often the most convenient. If you’re pressed for time to get into the Loop, the Jeffrey Express takes you into the heart of downtown in less than 12 minutes. Catch it, and other routes, at the bus terminal on 47th Street and Lake Park Avenue.

School’s in Session

Oakland neighborhood’s got plenty of great public and private schools to choose from, one in particular is the Donoghue Charter School (707 E 37th St, 773-729-5300). The University of Chicago’s Center for Urban School Improvement program showed a generous and heartfelt commitment to the neighborhood when they established the charter school in 2005. The Donoghue School opened its doors to community children so they could receive quality education with absolutely no tuition fees to worry about. The school accommodates up to 1,000 Chicago children in pre-kindergarten through 8th grades. Donoghue is located in the same historic building as the North Kenwood/Oakland Charter School and Ariel Academy, operated by Chicago Public Schools with the support of the University of Chicago. In addition to the following list of schools, you can find more information on Chicago area education facilities at our Chicago Guide Schools page.

Christ the King Lutheran School 3701 S Lake Park Ave – (773) 536-1984
Donoghue Charter School 707 E 37th St – (773) 729-5300
Jackie Robinson Elementary School 4225 S Lake Park Ave – (773) 535-1777
Lindblom College Prep High School 707 E 37th St – (773) 535-9300

Basic Needs

Can’t find your way around your neighborhood or the city? Don’t fret, the Chicago Transit Authority (CTA) buses and trains will get you where you need to go. If you’re planning an excursion out to the suburbs or Indiana get in touch with Metra Rail for all your travel planning.


Chicago Transit Authority (CTA) (888) 968-7282
Metra Electric Rail 312-322-6777


Mandrake Park 900 E Pershing Rd – (312) 747-7661


American Cuisine
Tastee Beef 4248 S Cottage Grove Ave – (773) 373-7089
Shark’s 4048 S Cottage Grove Ave – (773) 538-4889


New Age Chicago 4238 S Cottage Grove Ave – (773) 285-3765
Soul Salon 4256 S Cottage Grove Ave – (773) 268-3390

As one of the many diverse Chicago neighborhoods, Oakland offers homeowners a wide range of residential properties. Oakland homes include lofts, condos and townhomes, to name a few. In addition to Chicago real estate, you can get detailed neighborhood information from our comprehensive online Chicago neighborhoods guide. With features like dining, shopping, entertainment, and resources, we’ve done all the leg work already to make your home search that much easier. Now, when a listing in Oakland catches your eye, you can read all about the surrounding area and what it has to offer—all without setting foot in the neighborhood. Like a Yellow Pages, Metromix and MLS database all rolled into one, this site is your ultimate Chicago neighborhoods visitors’ guidebook.