Chicago, IL·District 299
Homes in the
Kennedy HS district.
Bungalow-lined, family-rooted Garfield Ridge: classic Southwest Side Chicago living minutes from Midway and a straight Orange Line ride to the Loop.
- Homes for sale
- 51
- Typical list
- $415,000
- Most expensive
- $769,999
- Most affordable
- $129,900
5324 Neva Avenue →
5586 Archer Avenue →
Crusaders · Royal Blue & Golden Yellow · 1,647 students · Chicago Public League
Active listings
51 homes on the market
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Market snapshot
The Kennedy HS area, by the numbers
Live MRED data, refreshed daily. What this market is actually doing right now, sales included, not a portal estimate.
Homes for sale now
59
Typical list price
$399,900
Avg time on market
8 days
Sold in the last year
63
Typical sale price · last 90 days
$345,000
Living near Kennedy HS
The area, not just the school
Garfield Ridge is one of those true Southwest Side Chicago neighborhoods where people put down roots and stay for generations. You will find block after block of well-kept Chicago bungalows and brick ranches, tidy front lawns, and quiet residential streets that feel a world away from the downtown bustle even though the Loop is only about ten miles northeast. It has long been a home base for working families, and that neighborly, settled character is a big part of the draw.
The location is hard to beat if you value getting around. Midway International Airport sits right at the edge of the area, so travel and airport-adjacent jobs are close at hand, and the Orange Line at Midway gives you a straight CTA ride into the Loop. Drivers have quick access to the Stevenson Expressway and Archer Avenue, the neighborhood's historic diagonal main street lined with shops, bakeries, and restaurants.
For buyers, the appeal is value and stability: solid, affordable single-family housing stock, a community-oriented feel, and parks and parish life woven through the blocks. It is a practical, family-friendly pocket of the city for anyone who wants space, a garage, and an easy commute without leaving Chicago.
🎓Grades 9-12
A four-year, coed Chicago Public Schools high school.
🌎IB since 2000
Kennedy has offered the International Baccalaureate program since 2000 and is an AVID school.
🛡️Crusaders
Teams compete as the Crusaders in the Chicago Public League, in royal blue and golden yellow.
👥~1,650 students
Enrollment was 1,647 for the 2024-2025 school year.
✈️By Midway
The school sits in Garfield Ridge, right beside Midway International Airport.
🚆Orange Line access
The CTA Orange Line at Midway offers a direct ride to the Loop.
The school
About John F. Kennedy High School
Kennedy High School opened on October 3, 1963, in the Garfield Ridge neighborhood on Chicago's southwest side, originally under the name John H. Kinzie High School. In 1965 the school was renamed to honor President John F. Kennedy, who had been assassinated in the year the school was founded. The school has been operated by Chicago Public Schools since its opening and remains a four-year, coed public high school serving grades 9 through 12.
Kennedy has been part of the International Baccalaureate program since 2000 and is an Advancement Via Individual Determination (AVID) school. Its program offerings include general education, the IB program, and special education services. The school's four-year graduation rate was reported at 89 percent for 2024-2025 on the Illinois Report Card.
Kennedy competes in the Chicago Public League and is a member of the Illinois High School Association, with varsity teams known as the Crusaders. The school fields fall, winter, and spring sports including football, soccer, volleyball, basketball, baseball, softball, cross country, wrestling, track and field, swimming, bowling, and water polo. Historically its strongest programs have been baseball, boys cross country, and girls bowling, with a string of City and Public League championships.
- District
- District 299
- Founded
- 1963
- Principal
- George Z. Szkapiak
- Conference
- Chicago Public League
- Address
- 6325 West 56th Street, Chicago, IL 60638
Notable alumni
- Donell Jones. R&B singer and songwriter.
- Jill Talley. Comedic actress and voice actor.
- Mark Protosevich. Screenwriter known for I Am Legend and Thor.
- Jim Hickey. Former Major League Baseball pitching coach.
Facts on this page sourced from Wikipedia and the District District 299 website. Last verified 2026-07-02.
Neighborhoods that feed Kennedy HS
Communities in the Kennedy HS area
Homes in these neighborhoods are zoned to Kennedy HS. Open one to see what is for sale there right now.
Listings filtered by the school the MRED listing agent assigned. Roughly 7 in 10 active listings have this field populated; the remaining listings will surface once the school-district boundary pipeline ships. School assignment is not a guarantee. Always verify with the district before writing an offer.
The questions buyers actually ask
Kennedy HS FAQ
The questions I get most from buyers shopping the Kennedy HS district. If yours isn't here, text 224-385-8779, same-day reply.
- Which neighborhood is Kennedy High School in?
- It is in Garfield Ridge on Chicago's far Southwest Side, about ten miles from the Loop and right beside Midway International Airport.
- What type of housing is common around the school?
- The area is known for classic Chicago bungalows and brick ranch and single-family homes, many built during the mid-20th-century growth years.
- How is the commute from this area?
- Midway International Airport is at the edge of the neighborhood, the CTA Orange Line runs into the Loop, and the Stevenson Expressway plus Archer Avenue give quick access across the region.
- Does Kennedy High School offer advanced academic programs?
- Yes. Kennedy has been an International Baccalaureate school since 2000 and is also an AVID school.
- How do I find homes near Kennedy High School?
- The listings here are filtered to homes whose MRED listing agent assigned Kennedy as the high school. Chicago is a choice-and-neighborhood district, so confirm enrollment options with CPS directly. For alerts on new homes in the area, text 224-385-8779.
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
- Pre-list improvements that pay back, and the ones that don't
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This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period July 21, 2025 through July 21, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.