Englewood has seen its share of both good fortune and hard luck over the years. Englewood Station was once a stop on the premier New York Central Railroad Line, and had one of the hottest shopping districts in the city. Unfortunately it suffered when many of the once-prominent industries, such as the railroad, left the community. Lately, though, there is a resurgence of interest in Englewood, as developers realize some of the hidden assets of the area, including convenient access to public transportation and expressways, loads of public parkland, and affordable housing. Not to mention free music concerts and outdoor films in the neighborhood's parks during the warm weather months.

Englewood Facts

Location: Approximately 7.5 miles south of the Loop
Bordering Neighborhoods: West Englewood, Back-of-the-Yards, Washington Park, Park Manor, Gresham
Boundaries: Garfield Boulevard (55th Street) to the north, State Street and Vincennes Avenue to the east, 75th Street to the south, and Ashland Avenue to the west.

Then and Now

Englewood Real Estate

The original inhabitants of the swampy prairie that is now Englewood were Mascouten Indians. In 1840 the United States Government Land Office in Chicago officially documented the land that is now Englewood as habitable and early settlers started to claim sections of the territory for building their homesteads. A nearby ridge became a well-used path by Native Americans and settlers alike, and over time the path grew into what is today Vincennes Avenue. One of the earliest residents reported looking south from what is now 66th Street and seeing nothing but wetlands for miles—a far cry from the multitude of houses and businesses that now occupy the terrain.

In the 1850s, railroad tracks were built that cut through Englewood, turning it into a major railroad hub known as the Chicago Junction. In the following years, the population of Englewood grew rapidly, and it was given a big shot in the arm as a result of the Chicago Fire. As the city was rebuilding, residents were forced to seek housing in more remote regions, and Englewood was one of the more attractive destinations because of its easy accessibility via train.

A few years after the fire, developers began laying out the foundation for a viable self-sufficient community between Wentworth Avenue and Halsted Street from 55th Street to 71st Street (present-day Englewood). Soon an increasing number of Swedish, German and Irish railroad workers, attracted by employment opportunities, started moving to the area from other nearby neighborhoods such as Bridgeport and Back-of-the-Yards.

By 1905 Englewood Station had become a crucial junction and passenger depot for three railroads: the Chicago, Rock Island and Pacific Railroad, the New York Central Railroad, and the Pennsylvania Railroad. It was perhaps most famous for the glamorous eastbound streamliner trains such as the 20th Century Limited and the Broadway Limited, which were synonymous with style, speed and grace, and provided the most luxurious means of traveling between Chicago and New York City. At its peak as a station in 1928, more than 1,000 passengers a day traveled through Englewood.

In the roaring 1920s, Englewood’s shopping district at Halsted and 63rd streets was the city’s second busiest shopping district, only topped by the Loop. By the end of the decade, Sears had established a $1.5 million department store there. Sadly, the ensuing stock market crash had a severe impact on the prosperity of the high-flying neighborhood, and in many ways it never recovered.

The ensuing years after World War II saw increasing stratification, as many of Englewood’s Irish, Swedish and German residents headed to other neighborhoods. The 'Great Migration' of African Americans from the South brought a surge of new black residents to the area, and by 1950 the population of the neighborhood was about 10 percent African American. Many more families moved to Englewood in the late-1950s when large construction projects such as the Dan Ryan Expressway displaced thousands of residents on the south side.

During the 1960s, in an attempt to inject the neighborhood with a commercial revitalization, Chicago officials commissioned the building of a pedestrian mall in Englewood at Halsted and 63rd streets. In the end, the attempt was a failed one, and critics of the project claimed that rather than creating more business, it actually precipitated a decline in small retail stores that had been in the neighborhood for years. Many of those small stores did return, but it was too late. In the 1980s the shopping center struggled as it lost almost all of its anchor stores—Wieboldt’s, Sears and others closed their doors or relocated elsewhere. The mall became a hodgepodge of smaller specialty shops that sell wigs, clothing, shoes, groceries and the like.

The pedestrian mall—much like the State Street mall in the Loop—was abandoned as a failed idea in the late 1980s, and Halsted Street was once again opened to traffic at 63rd Street. In 1999, Mayor Richard M. Daley announced a $256 million revitalization plan for Englewood, which included a new police station, housing, and the relocation of Kennedy-King College from 6800 Wentworth Avenue to a 40-acre site at 63rd and Halsted streets, in the heart of Englewood. With the ensuing changes initiated by Kennedy-King’s emergence on the scene, the neighborhood now has some renewed interest in its real estate. What many had long considered a blighted community has recently become an area with a strong base for future growth.


Similar to the Back-of-the-Yards neighborhood to the north, Englewood is blessed with a great variety of green space indebted to its industrial roots, when a number of social activists banded together to use parks and recreational activities to solve some of the societal ills of the early 20th century, including poverty, unsanitary living conditions and overcrowding.

One of these early public commons was Ogden Park (6500 S. Racine Ave., 312-747-6572). Named for Chicago's first mayor William B. Ogden (1805-1877), the park was unveiled on the centennial of Ogden's birth. Today, you can play a game of baseball or softball on one of the diamonds, go swimming in the outdoor pool, head indoors to play a game of hoops in the gymnasium, or work out on the weight lifting machines in the fitness center. If you need a place for a community meeting, there are meeting rooms available as well as assembly halls for larger groups. Join the throngs of bikers and joggers on the park’s paths in the summer, or hit the tennis courts for a game.

Another park established in the Englewood neighborhood by the South Park Commission in the early 20th century was Hamilton Park (513 W. 72nd St., 312-747-6174). Nationally renowned landscape architects the Olmsted Brothers (famous for Central Park in New York City) and members from Daniel Burnham’s architectural firm designed the entire system of new parks that were planned for the city around this time period, including both Englewood’s Hamilton and Ogden parks. Hamilton Park was named for Alexander Hamilton (1755-1804), advisor to George Washington and first secretary of the U.S. Treasury who was killed in a duel with Aaron Burr. To this day there is still an extensive mural in the Hamilton Park fieldhouse honoring past United States presidents and administrations. But enough with the history lesson.

There is plenty of space to relax under the trees in the summer at Hamilton Park, and maybe take in a baseball or softball game on one of the many diamonds. Paths for bicycling, jogging or walking circle the grounds, and a spray pool for the kids to cool off during those scorching August days is onsite too. During the summer months there are also free concerts by various musicians. When the weather turns cooler, the fieldhouse is equipped with exercise equipment and free weights, and there are meeting rooms available for your book club or other Englewood neighborhood get-togethers.

Located across the street from Sherwood School, the parks department used to flood the field of Sherwood Park (5701 S Shields Ave., 773-256-0926) for ice skating in the winter. There’s no longer any ice skating, but the park is a vibrant destination alive with activity. It has been expanded twice, and includes a baseball/softball diamond, and a shelter perfect for picnicking. There is an indoor gymnasium with volleyball and basketball facilities and a water playground for the kids.

In addition to the three major parks in Englewood, there are also several smaller playlots tucked in among the residential streets, including Moran Playground Park (5727 S Racine Ave., 312-747-6560), which was named for Terrance F. Moran, alderman of the 16th ward (which includes Englewood) from 1923 to 1937. The city has made dozens of improvements since the park was first created in 1926, including expanding the long rectangular property, planting trees, shrubs, and grassy areas at the extreme ends, and installing a playing field, playground equipment, and a recreation building in the center of the park. Over the years a spray pool was added and, for those who like to hoop it up, a basketball court was added in 1993. If your kids are aspiring Major Leaguers, be sure to take advantage of the summer Cubs Care Rookie Baseball league, which includes free clinics for beginners. Moran Park also participates in the Chicago Park District’s Movies in the Park program (again, we’ll get into this more later—so keep reading!).

Even before Englewood was a part of the city, Lily Gardens Park (632 W. 71st St.) existed, attracting residents to its lovely flowering setting for leisure time activities and peaceful afternoon strolls. Its establishment dates back to 1886—the year the city annexed Englewood—when a group of developers dedicated the property as park space. Originally known as 72nd Street Park, by 1910 the park had been designated The Lily Gardens, which referred to the park’s two impressive basins planted with water lilies. Unfortunate difficulties in maintaining the lily ponds led the park district to replace them with a playground. These days, the little ones have a blast on the slides and swings and get silly on the rope and timber fort-like climbing structure. One of Englewood neighborhood’s most recent additions to its plentiful park space is Periwinkle Playlot Park (30 W. Marquette Road), which was created in 1973, and provides much-needed playground facilities for the Greater Grand Crossing area in Englewood. The park takes its name from the periwinkle plant, which has been used to make vinblastine, a treatment for childhood leukemia. Parents bring their kids here to monkey around on the monkey bars, hit the slide or climb around on the jungle gym equipment.

Englewood Real Estate

The majority of housing options in Englewood are single-family dwellings, although there are several vintage-style condominium buildings, townhomes, and half-duplexes in the neighborhood as well. Residents find Englewood’s location convenient for transportation as both the CTA rapid transit and the Dan Ryan Expressway run right through the area. It’s true this south side Chicago community has seen its share of problems in the past, but recently the neighborhood has been on the upswing.

There are pockets of new two-story houses slated for construction in Englewood. These brick exterior homes are similar in style and provide ample living space for families with four bedrooms and a price in the upper $200,000s. The rest of the neighborhood is a mixture of detached homes, many with garage parking and modest private yards. Although some streets are pockmarked with empty lots and abandoned buildings, you’ll also see plenty of well-maintained large two-stories, raised ranches, split levels, simple frame houses, and classic Chicago bungalows throughout Englewood’s residential subdivisions.

And don’t forget, there are lots of great parks nearby, which have been a big draw for families. Plus, anyone who is willing to put a little elbow grease into their home will discover a number of properties that need restoring and renovation, or empty lots that offer the opportunity for brand new construction if you’d rather start from the ground up.

The price for a three-bedroom single-family home in Englewood ranges from $45,000 for one of those fixer-uppers, to $350,000 for a vintage two-story detached townhouse that is in good condition or a newly built property. Larger homes that have four to five bedrooms start around $50,000, but the high end goes up to just under $300,000—again, for new construction residences. For multi-unit housing, prices start around $50,000 for a two-bedroom townhome and go up to the mid-$200,000s for a place with three or four bedrooms.

What’s on the Menu?

Whether you’re looking for good barbecue or a tasty sandwich, Englewood neighborhood has a good selection of food, especially for breakfast or lunch.

If you love good gizzards (and really, who doesn’t?), then The Original Leon’s Bar-B-Q (1200 W. 59th St., 773-778 7828) is the place for you. Mississippi-native Leon Finney started the business with his aunt in 1940, and the Finney family is still dishing up the barbecue today right in the heart of Englewood neighborhood. The recipe hasn’t changed for 70 years now, so they must be doing something right. Beyond the gizzards, Leon’s serves up daily specialties, including hickory-smoked spareribs, rib tips and hot links, all accompanied by Leon’s tangy-sweet barbecue sauce. When Englewood locals are craving a quick meal of fried catfish, perch or whitefish, there’s only one place to go: Hook Fish & Chicken (810 W. 59th St., 773-488-6666). This is good food done fast and you can eat-in or carryout. For just a quick snack, try the hush puppies or stuffed jalapenos. They also have hot and spicy buffalo chicken wings. Challenging Hook Fish & Chicken for wing supremacy, however, is, surprisingly, Pete’s Italian Beef (7352 S. Halsted St., 773-488-3406). Some will argue that these are the best hot wings in town, and we are certainly hard pressed to find any that are cheaper. For under $4 you get eight hot wings, bread and a soft drink. In addition to the wings, Pete’s does have very good Italian beef—as you might have imagined. The surroundings are strictly minimalist with a small dining room, but it’s a great place to grab a quick lunch.

Spot Chicken Fish & Pizza (901 W. 59th St., 773-651-6982) serves up some of the best fried chicken in town. Seriously! They claim the secret is using a buttermilk batter that makes everything incredibly crispy and incredibly tasty—not to mention, incredibly bad for you. But as long as we don’t eat here everyday, and maybe do a few extra sit-ups before dining at The Spot, that buttermilk recipe is A.O.K. with us. Not a poultry fan? Then try the fish, it’s also very good, of course, as it is listed in the restaurant’s name. And if you visit during midday, make sure to get one of the lunchtime combination platters, including either fish or chicken, choice of side and a soft drink, all for only $6.99.

Mark Your Calendar

When we can’t take another minute of being inside the house on a stuffy summer night, we head over to Moran Playground Park (5727 S. Racine Ave., 312-747-6560) around dusk to catch one of the films being shown outdoors during the Chicago Park District’s "Movies in the Park" series. The shows are free and appropriate for all ages, so it’s common to see entire Englewood families packing into the park for a viewing on the big screen under the stars. Just remember to bring the popcorn, a blanket or some lawn chairs, and a cooler for the drinks, and you’ve got yourself a nice outing that doesn’t cost a thing and that the whole family will love. Of course, if you don’t mind sitting on the grass and don’t feel like snacking, you won’t need to bring anything—talk about enjoying the simple life!

Hamilton Park (513 W. 72nd St., 312-747-6174) hosts dozens of free concerts throughout the summer, ranging from drum circles to classical quartets. Whether you love salsa or pop, big band music or the blues, there is definitely a concert you’re sure to appreciate somewhere in the lineup. Past concerts in the park have included The Peaches Staten Blues Band, the distinctive folk honky-tonk of the Hoyle Brothers, and the swinging percussion of Jose Valdes and the Latin Jazztets, who have been described as samba with sax.

The Englewood Community Cultural Planning Council (7424 S. Normal Avenue, 312 362-6524) works with the surrounding community to provide artistic programs including concerts and art exhibitions throughout the year. One of the most intriguing events in recent memory held at the Hamilton Park fieldhouse was Drum Dialogue. This workshop, hosted by vocalist, percussionist and storyteller Glenda Baker, presents poems to the beat of rhythmic drumming. The goal of the program is to bring those unfamiliar with poetry and percussion together with expert musicians for an evening of fun and creativity in an enlightened atmosphere.

Getting Around

A bevy of CTA 'El' lines (Chicago’s train system that runs partially on elevated tracks throughout the city) and a number of CTA bus routes serves the Englewood community. And if you’re driving, the neighborhood offers multiple entrances to Chicago’s most extensive expressway, making any destination just a quick trip away.

In Englewood, if you have your own car you’ll be pleased to know there is plenty of street parking on Ashland Avenue, Garfield Boulevard (55th Street), and 63rd Street, which are the main thoroughfares that frame the center of the community, and generally it’s not too difficult to find a spot. Be careful to read any nearby posted signs about restrictions, particularly street cleaning days because those tickets are no joke. Side street parking in Englewood is plentiful as well, but again, check for any limitations to avoid that nasty orange envelope resting on your windshield when you return to your vehicle.

If you’re driving, the neighborhood is accessible from I-55 (Stevenson Expressway) using the Damen Avenue exit. From there travel south to Pershing Road (you have to make a bit of a detour around the railroad yards here). Then head east until you hit Ashland Avenue, and finally go south until you pass Garfield Boulevard (you can’t miss it; it’s the one with all the trees down the center). This route can be tricky if you’re not familiar with the area, so another way to get to Englewood, which is much more direct, is to arrive via I-90/94 (Dan Ryan Expressway) using the 59th Street exit. The Dan Ryan runs right through the neighborhood, so once you get off the expressway you are right there.

CTA bus lines form a patchwork through Englewood and serve just about every part of the city. We find the #55 and #55X (express) to be very efficient when traveling about the neighborhood. The #55 buses take passengers eastbound on Garfield Boulevard and connect with the #29 northbound at State Street, which heads right into the Loop. Or, if you want to take in the new exhibit at the Museum of Science and Industry, stay on the #55 and ride it all the way to the end of the line at the Museum Campus. If you’re jetting out of town, take the #63 westbound on 63rd Street to Midway Airport. Over on Halsted Street, the #8 bus runs northbound all the way to Addison Street in Wrigleyville and southbound to 79th Street.

The CTA Green Line and Red Line trains are also popular options for public transportation within Englewood and to destinations throughout the city. The two Green Line stations in the neighborhood are both on 63rd Street with one at Ashland Avenue and the other at Halsted Street. These are the last two stations on the line, but if you get on here, you can take the train north, straight to downtown. Also heading north to the Loop, the Red Line runs in the median of the Dan Ryan Expressway and has stops in Englewood at 69th Street, 63rd Street and Garfield Boulevard.

School’s in Session

Englewood has a substantial selection of both public and private schools available right in the neighborhood where local kids can head off to class. In addition to the following list, you can find more information on Chicago area schools at our Chicago Guide Schools page.

Stagg Elementary School – 7424 S Morgan St. – (773) 535-3565
Bontemps Elementary School – 1241 W 58th St. – (773) 535-9175
Copernicus Elementary School – 6010 S Throop St. – (773) 535-9180
Nicholson School for Science and Math – 6006 S Peoria St. – (773) 535-3285
Englewood High School – 6201 S Stewart Ave. – (773) 535-3600
Reed Elementary School – 6350 S Stewart Ave. – (773) 535-3075
Kershaw Elementary School – 6450 S Lowe Ave. – (773) 535-3050
Bass School – 1140 W 66th St. – (773) 535-3275
Banneker Elementary School – 6656 S Normal Blvd. – (773) 535-3020
Wentworth Elementary School – 6950 S Sangamon St. – (773) 535-3394
Yale Elementary School – 7025 S Princeton Ave. – (773) 535-3190
Ralph Bunche Elementary School – 6515 S Ashland Ave. – (773) 535-9060
Altgeld Elementary School – 1340 W 71st St. – (773) 535-3250

Basic Needs

Englewood is one of the larger Chicago neighborhoods that supplies residents with a good number of establishments and services to suffice those everyday needs. To give you an idea of what you can expect to find, we’ve compiled a helpful list of some of the places you can get your bare necessities, from jam and bread to hair gel and make-up.

Public Library Branch (Sherman Park) – 5440 S. Racine Ave. – (312) 747-0477
Chicago Transit Authority – (888) 968-7282
Post Office (Englewood) – 611 W. 63rd St.


Randolph Pharmacy – 5500 S. Damen Ave. – (773) 434-7186
Rolex Pharmacy – 6032 S. Halsted St. – (773) 994-7762
Mall Pharmacy – 6202 S. Halsted St. – (773) 874-7400

Hospital Emergency Room

St. Bernard Hospital – 326 W. 64th St. – (773) 962-3900

Grocery Stores

Wood Food Mart – 5600 S. Wood St. – (773) 436-4122
Ashland Supermarket – 5659 S. Ashland Ave. – (773) 436-4420
Gateway Market – 5601 S. Halsted St. – (773) 846-5731
59 Prime Meat Market – 724 W. 59th St. – (773) 783-8888
Big E Grocery – 5905 S. Halsted St. – (773) 873-9171
Sharif Food & Liquor – 5960 S. Racine Ave. – (773) 925-5500
R & F Food & Liquor – 6057 S. Racine Ave. – (773) 776-2497


Curves – 806 E. 78th St. – (773) 874-4601


Carpenter Playlot Park – 6153 S Carpenter St
Edmonds Playlot Park – 711 W 60th Pl
Emerald Playlot Park – 5600 S Emerald Ave
Hamilton Park – 513 W 72nd St – (312) 747-6174
Harris (Ryan) Memorial Park – 6781 S Lowe Ave.
Junction Grove Playlot Park – 345 W 64th St.
Lily Gardens Park – 632 W 71st St
Lowe Playground Park – 5203 S Lowe Ave – (312) 747-6445
Luna Playlot Park – 5558 S Green St
Malus Playlot Park – 5426 S Shields Ave ( – 312) 747-6136
Memorial Playlot Park – 149 W 73rd St
Ogden Park – 6500 S Racine Ave – 312-747-6572
Periwinkle Playlot Park – 30 W Marquette Rd
Sherman Park – 1301 W 52nd St – (312) 747-6672
Sherwood Park – 5701 S Shields Ave – (773) 256-0926

Movies in the Park: Moran Playground Park – 5727 S. Racine Ave. – (312) 747-6560
Englewood Community Cultural Planning Council – 7424 S. Normal Ave – (312) 362-6524


Garfield Discount – 1558 W. 63rd St. – (773) 918-0811


Lee’s E T Lounge – 5610 S. Ashland Ave. – (773) 471-5482
Lloyd’s Lounge – 6046 S. Racine Ave. – (773) 778-6656
Taste Entertainment – 6331 S. Lowe Ave. – (773) 873-6700
Keynote Lounge – 1116 W. 63rd St. – (773) 436-5220
Orchard Place of Englewood – 6344 S. Peoria St. – (773) 488-4999
Poor Roy’s Lounge – 6759 S. Ashland Ave. – (773) 434-2315
Hot City Cocktail Lounge – 7432 S. Racine Ave. – (773) 224-9583
The Family Lounge – 6946 S. Racine Ave. – (773) 783-4017
New Generations Lounge – 754 W. 74th St. – (773) 783-1167


Art’s Restaurant – 7401 S. Ashland Ave. – (773) 488-1222
Catfish City – 7340 S. Racine Ave. – (773) 483-5492
Lezetta’s Restaurant – 6049 S. Halsted St. – (773) 487-5563

Scott T’s Barbeque – 5521 S. Ashland Ave. – (773) 471-1989
Blacks BBQ Sandwiches – 516 W. 71st St. – (773) 651-3066
The Original Leon’s Bar-B-Q 1200 W. 59th St. (773) 778-7828

B & B Pizza King – 4 W. Garfield Blvd. – (773) 373-5464

Fast Food
Hook Fish & Chicken – 810 W. 59th St. – (773) 488-6666
The Spot Chicken Fish & Pizza – 901 W. 59th St. – (773) 651-6982
KFC – 844 W 63rd St. – (773) 651-1995
Brothers Submarine – 1158 W. 63rd St. – (773) 476-6282
Church’s Fried Chicken – 6600 S. Halsted St. – (773) 783-1153
White Castle – 6646 S. Halsted St. – (773) 873-1855
Island Fish & Chicken – 6701 S. Racine Ave. – (773) 994-2201
Chicago Submarine – 7201 S. Ashland Ave. – (773) 783-9193
Pete’s Italian Beef – 7352 S. Halsted St. – (773) 488-3406
Maxwell Street Grill – 7445 S. State St. – (773) 487-7445
Popeye’s Famous Fried Chicken & Biscuits – 5541 S. Wentworth Ave. – (773) 924-6200
Burger King – 6900 S Halsted St. – (773) 651-1423
Supreme Fish Hoagy – 5506 S. Ashland Ave. – (773) 925-6720
Englewood Subs & Grill – 5901 S. Morgan St. – (773) 436-5512
Tedro’s – 1055 W. 63rd St. – (773) 918-1467
Jad Best Foods – 6645 S. Halsted St. – (773) 994-4857

Chinese Cuisine
Yummy Chinese Kitchen – 735 W. 63rd St. – (773) 994-4111

Sometimes it makes more sense to view the city of Chicago as a bunch of separate neighborhoods, especially when it comes to real estate. Whether you are in the market for a loft, condo, townhome, or house, it is just as important to inspect the surrounding area as it is to inspect the home’s foundation. Englewood neighborhood is just one Chicago community with an abundance of residential properties, and a life all its own. From where you send your kids to school to where you dine at night, the information we provide is an essential piece of the puzzle when you’re trying to decide whether or not to buy that beautiful loft or adorable house in Englewood.