Jackson Park Highlands

Jackson Park Highlands, one of the most historic and attractive neighborhoods in the south side of Chicago, is situated in a small pocket of the larger South Shore community that rests next door to scenic Jackson Park. Beautiful Victorian era mansions are commonplace in Jackson Park Highlands. Instead of tightly-packed rows of houses, these grand homes are spread out atop oversized green grass lots with matured trees and privacy hedges separating the properties even more. Not all real estate in Jackson Park Highlands is up market, there are also very nice mid-century split-levels and redbrick courtyard condominiums that provide ample living space for couples and families with smaller budgets.

Jackson Park Highlands Facts

Location: Approximately 10 miles south of the Loop
Bordering Neighborhoods: South Shore, Woodlawn, Grand Crossing
Boundaries: Jeffery Boulevard the east, 67th Street to the north, 71st Street to the south and Cregier Avenue to the west.
Crime Statistics: Go to CLEARMap for crime stats on specific Chicago neighborhood, intersection, address or police beat.

Then and Now

Jackson Park Highlands Real EstateThe history of Jackson Park Highlands is a classic story of gentrification on Chicago’s south side. Like most of the surrounding area, the fate of Jackson Park Highlands was intimately linked to the success of the World’s Columbian Exposition that was held just to the north in Hyde Park in 1893. The neighborhood had only been annexed by the city of Chicago about four years prior to the World’s Fair, so at the time it was still little more than a near south suburb.

The Columbian Exposition was a resounding success, drawing more than 25 million visitors to the region. With dramatic increases in both traffic and attention, property values in the South Shore region appreciated dramatically. The development of Jackson Park Highlands, however, did not result from raising property values; instead, it was the result of Protestant 'white flight' from the nearby Washington Park neighborhood that was faced with a large influx of African American families who were moving to the Chicago area from the South. The Protestants started developing and settling the land in Jackson Park Highlands between the turn of the century and 1905, carefully crafting it as an exclusive oasis on the southern edge of the sprawling grounds of Jackson Park.

In 1906, the residents of Jackson Park Highlands opened the South Shore Country Club, a garish and fancy complex located on a 67-acre plot of lakeshore property. The exterior of the country club was designed in Mediterranean Revival style, an architectural genre rarely seen in the Midwest. The club was built by the Marshall & Fox firm, which is also credited with the Blackstone Hotel and the Drake Hotel in downtown Chicago. The man that conceived of the resort, Lawrence Heyworth, had the good fortune of timing the club’s opening with the closing of another golf course in nearby Washington Park. As a result, Heyworth had little trouble gaining enough money and public support to go through with the project.

Jackson Park Highlands is a place of single-family homes a lot like neighboring Hyde Park or Kenwood. In the decade after the Jackson Park settlement was formed, all of the South Shore community experienced an influx of new arrivals and a subsequent housing boom. The area was populated by middle and working-class Jews and African Americans, as well as Irish, Swedish and German immigrants. The South Shore boom bolstered the seclusion of the Jackson Park highlands community, as the neighborhood was nicer and its residents were considerably wealthier than those moving into the surrounding neighborhood. That status has continued throughout the 20th century, as several famous Chicagoans have lived in Jackson Park Highlands, including activist Reverend Jesse Jackson, rocker Bo Diddly, and pro football player Gale Sayers.


Jackson Park, the third largest park in the city of Chicago, serves as the northern border to the Jackson Park Highlands neighborhood. The land was originally owned by Mary Jackson—the cousin of seventh president Andrew Jackson—who sold the land to the city of Chicago in the 1870s. Fredrick Law Olmsted (the chief architect of Central Park in New York) designed the park as the site for the World’s Columbian Exposition which was held in 1893. It served as the fair’s foundation and was therefore built on a grand scale with great ambition and gusto behind its creation. Jackson Park is a vast 500-acre recreation area with a large system of lagoons cutting through the landscape. There are numerous scenic trails that run through the grounds for walking, jogging, and biking.

One of the most popular attractions in the park is the Osaka Garden, a tranquil Japanese garden located on a wooded island flanked by the middle of the east and west lagoons. And perhaps the most relevant feature to Jackson Park Highlanders is the 18-hole golf course situated on the southern portion of Jackson Park. Brush up on that swing, head next door and take to the links for friendly game with work buddies or a crew from the neighborhood.

Jackson Park Highlands Real Estate

As a result of its historically exclusive status, today the tree-lined residential streets of Jackson Park Highlands offer some of Chicago’s largest and most attractive properties in the city. Of course, with the prestige of living in such an elegant neighborhood, homebuyers can expect the real estate here to be some of the more expensive on the south side.

The immense detached single-family dwellings that sit on large green lots are most common in the neighborhood, although several low-rise condo and apartment buildings were erected in the area in the 1950s and ‘60s. The main multi-unit residential buildings are mostly along Jackson Park Highlands’ wide border thoroughfares. The massive vintage-style, redbrick courtyard condominiums typically offer one-, two-, and three-bedroom units that range in price from to the mid $100,000s to the low $200,000s.

Several of Jackson Park Highlands’ beautiful houses, built in the early 1900s, would be considered mansions by today’s standards and continue to maintain the awe-inspiring grandeur. One of the great design approaches used by the architects of the neighborhood’s residences of the time period was to construct these homes set back on 50-foot-wide plots of land leaving generous front lawn space and room for faultlessly trimmed hedges and wrought-iron front gates. Such features were innovative at the time, and were later incorporated into typical suburban neighborhood planning. Other infrastructural advancements enjoyed by the residents of Jackson Park Highlands back in its emergence were the use of underground utilities and—most notably—it is one of the only Chicago neighborhoods that doesn’t have alleys between streets.

There is a wide variety of homes in the Jackson Park Highlands that span from towering three-story Victorians with room-size pillared porches and back garages to more modern split-levels with attached garages. All in all, the properties in this once elite south side Chicago neighborhood are impressively magnificent with a timeless charm that persists throughout the years. Detached single-family houses in Jackson Park Highlands start in the low $300,000s, but the price tag for many of these century-old homes can easily be in the $700,000 or $800,000 range.

Getting Around

Jackson Park Highlands is small in area, so getting around the neighborhood doesn’t pose much problem. With a few retail shops and eateries along 71st Street, which bounds the community to the south, and the golf course to the north, everything here is less than five blocks from each other. We prefer to walk if the weather is nice, but during a winter snowstorm or on those rainy spring afternoons, it’s just as easy to hop in your car and shoot over to the local E&M Food market (1908 E 71st St, 773-667-1546) for those few necessities or swing by Red Pagoda (1918 E 71st St, 773-684-3580) for some carryout as there’s plenty of street parking options for quick errands.

Sadly, no CTA 'El' trains connect the Jackson Park Highlands to the rest of Chicago; however, there are a number of other public transportation alternatives that allow residents to get where they need to go. For one, the Metra Electric line, which stops in the neighborhood’s southwest corner at Stoney Island and 71st Street, is the most direct—and probably the most comfortable—way of getting to and from downtown Chicago. The trains, which run on a fixed schedule, travel directly to Hyde Park and on to South Water Street (beneath Millennium Park) in Chicago. If you miss the Metra, though, CTA buses service Jackson Park Highlands as well, so check out the map online or at the station to see which one provide the best route for where you want to go.

If you’ve got a car, and most people in Jackson Parks Highland do, the neighborhood is very accessible to the rest of Chicago due to its proximity to scenic Lake Shore Drive which begins just north in Jackson Park and follows the shoreline along the water’s edge up past downtown and on to Chicago’s northern neighborhoods. Entrances to the Dan Ryan Expressway (I-90/94) lie to the west and provide another alternative for traveling by vehicle to any destination in the city.

Basic Needs

Jackson Park Highlands is pretty tiny and doesn’t have the most extensive list of neighborhood amenities, but residents can still get those bare essentials at the local establishments, just blocks from their front door.

Grocery Stores

E&M Food - 1908 E 71st St - (773) 667-1546


Payless Shoe Source - 2000 E 71st St - (773) 684-0826
Wilson Bros Paint & Hardware - 1914 E 71st St - (773) 363-9066


Asian Cuisine
Red Pagoda - 1918 E 71st St - (773) 684-3580

Deserts/Ice Cream
Taurus Express - 1904 E 71st St - (773) 363-6403

There’s a lot of mystery involved in searching for a new home-it starts with the property and expands outward to encompass the street, the block, the neighborhood, the entire city! Every little thing matters from the color of the walls to the attractions of the town. That’s why a guide like this one on Jackson Park Highlands is so helpful to potential homebuyers. Without leaving the comfort of your desktop computer or laptop, you’ve got an extensive pool of information on all of Chicago’s neighborhoods that includes first-hand descriptions of dining, entertainment, shopping, bars, and events, in addition to lists of schools, hospitals, post offices, and gyms. We’ve done all the research to carefully craft this one-stop online spot, and create your hub for the real deal on Jackson Park Highlands. So as soon as a Chicago loft, condo, townhome or house catches your eye, you know where to come for the low down on the digs around that prime piece of real estate.