20 Chicago Suburbs With The Most Expensive Homes: Luxury Living Outside The Windy City

Nestled outside the bustling city of Chicago are suburbs that boast more than just serene streets and community-centric amenities—they’re home to some of the priciest real estate in the state. From sprawling estates to luxurious lakefront properties, these suburbs attract homebuyers seeking exclusivity, grandeur, and high-end living.

But which suburbs truly top the list when it comes to expensive homes? We’ve done the research to provide you with a glimpse into the lavish lifestyles these communities have to offer. Whether you’re dreaming of upgrading to a luxury home, curious about Chicago’s affluent neighborhoods, or simply fascinated by high-end real estate trends, you’re in the right place.

Why Are Chicago Suburbs in Demand?

The Chicago suburbs have long attracted those seeking a balance of urban and suburban lifestyles. With proximity to the city’s rich culture, job opportunities, and amenities, these suburbs offer the perfect combination of convenience and tranquility.

But for luxury buyers, these areas provide additional perks, such as sprawling properties, proximity to private schools, exclusive country clubs, and vibrant local dining scenes. This blend of amenities and community charm has cemented the Chicago suburbs’ status as a hub for high-end living.

Let’s explore the suburbs that stand out for their premium home and real estate offerings.

1. Winnetka

Winnetka takes the crown as one of the most prestigious suburbs in the Chicago area. Known for its tree-lined streets and proximity to Lake Michigan, this North Shore gem oozes elegance.

Median Home Price

The median home price in Winnetka hovers around $1.75 million, with many homes easily selling for upwards of $4 million, especially those closer to the lake.

Why It’s Pricey

• Lakefront Estates: These properties offer exclusive private beaches and breathtaking waterfront views, providing residents with a serene and luxurious living experience. The allure of living along the lakefront, combined with privacy and picturesque landscapes, makes these estates highly sought after.
• Top-Tier Schools: The area boasts exceptional public schools, with New Trier High School consistently ranking among the best in the nation. These schools offer comprehensive academic programs and a variety of extracurricular activities, ensuring students receive a well-rounded education that prepares them for future success.
• Architectural Charm: The neighborhood features a stunning array of homes, ranging from Colonial to Tudor-style architecture. Each residence is uniquely designed with exquisite craftsmanship, showcasing historical charm and character that is both captivating and timeless. This architectural diversity adds to the area’s distinctive appeal.

Winnetka School District

Winnetka Public Schools District 36 serves Winnetka, Illinois, offering top-tier education for students from junior kindergarten through eighth grade. The district includes five schools: Crow Island, Greeley, and Hubbard Woods elementary schools (grades JK-4), The Skokie School (grades 5-6), and Carleton Washburne School (grades 7-8). Known for its progressive approach and academic excellence, District 36 ranks among the nation’s top school districts. Its differentiated instruction model tailors learning to each student’s needs, fostering intellectual curiosity and social-emotional growth. With a reputation for innovation and high achievement, the district is a cornerstone of the Winnetka community, attracting families seeking exceptional public education. Graduates go on to attend the highly-regarded New Trier Township High School.

2. Kenilworth

With a tiny population of just under 2,500, Kenilworth is as exclusive as it gets. Often called the most affluent suburb in Illinois, Kenilworth is known for its quiet streets and serene atmosphere.

Median Home Price

The median home price sits at nearly $2 million, making it one of the most expensive suburbs not just in Illinois but in the entire Midwest.

Why It’s Pricey

• Privacy and Space: Kenilworth offers larger lot sizes and a low-density population, which are particularly appealing to those seeking privacy and tranquility away from the hustle and bustle of city life. This serene environment allows residents to enjoy spacious yards and a more secluded living experience.
• Historic Homes: The village is renowned for its historic homes, many of which date back to the early 1900s. These residences showcase stunning craftsmanship and architectural details, reflecting a rich history and timeless elegance that attract admirers of classic design and heritage.
• Easy City Access: Despite its peaceful ambiance, Kenilworth is conveniently located just 17 miles north of downtown Chicago. This proximity allows for a short and manageable commute, making it an ideal location for those who work in the city but wish to reside in a quieter, suburban setting.

Kenilworth School District

Kenilworth School District 38 serves the village of Kenilworth, Illinois, providing an exceptional education within a single, historic institution: The Joseph Sears School. This unique K-8 structure fosters a deeply connected and supportive learning community. The district is nationally recognized for its academic rigor, innovative programming, and consistent high performance on standardized assessments. District 38 is committed to personalized learning, ensuring that each student is challenged and supported through a robust curriculum emphasizing core academics, arts, and character development. With very small class sizes and a strong community-school partnership, it maintains a reputation as one of the premier public school districts in the state. Graduates matriculate to the acclaimed New Trier Township High School.

3. Glencoe

Glencoe offers a picturesque setting right along Lake Michigan’s shores. It’s a prime spot for those who seek luxury living with a focus on nature and outdoor activities.

Median Home Price

The average home in Glencoe sells for around $1.4 million, though prices can soar to over $5 million for waterfront properties.

Why It’s Pricey

• Outdoor Appeal: The Chicago Botanic Garden and scenic walking trails are local highlights, offering residents a chance to connect with nature and enjoy picturesque landscapes year-round. Whether it’s a peaceful stroll or an energetic hike, the area provides a serene escape from the hustle and bustle of city life.
• Community Features: Premium country clubs and high-profile neighbors are staples of Glencoe living, providing an environment of sophistication and camaraderie. The clubs in the Glencoe area offer a range of activities, from golf to gourmet dining, allowing residents to cultivate both leisure and networking opportunities.
• Architectural Range: From modern builds to timeless classics, there’s something for every luxury buyer, with homes that boast exceptional design and craftsmanship. The diverse architecture reflects the unique tastes and lifestyles of its residents, making it a coveted area for those seeking a distinctive and high-end living experience.

Glencoe School District

Glencoe School District 35 serves the village of Glencoe, Illinois, providing a distinguished public education for students from kindergarten through eighth grade. The district operates three developmentally focused schools: South School (Grades K-2), West School (Grades 3-4), and Central School (Grades 5-8). This grade-level center approach allows educators to tailor instruction precisely to the developmental needs of each age group. District 35 is recognized for its rigorous academic standards, strong emphasis on social-emotional learning, and robust arts programming. Consistently ranking among the state’s top-performing districts, it fosters a culture of excellence and innovation. Graduates matriculate to the highly acclaimed New Trier Township High School, continuing their path of superior academic achievement.

4. Highland Park

Home to a blend of old-world charm and contemporary luxury, Highland Park has long been a suburb synonymous with affluence.

Median Home Price

Highland Park’s median home price is approximately $750,000, but lakefront mansions can easily exceed $10 million.

Why It’s Pricey

• Cultural Richness: Ravinia Festival, the area’s renowned outdoor concert venue, attracts thousands of visitors yearly with its diverse lineup of performances ranging from classical to contemporary music, making it a cultural cornerstone of the community.
• Lakefront Properties: Expansive estates with private beaches contribute to the high property values in this area. These luxurious homes often feature stunning views of Lake Michigan, adding to their desirability.
• Movie-Magic Appeal: Highland Park has served as the backdrop for numerous films, including the iconic Home Alone. This connection to Hollywood not only enhances its reputation but also adds a unique charm that draws interest from fans and filmmakers alike.

Highland Park School District

North Shore School District 112 serves the community of Highland Park, providing comprehensive public education from pre-kindergarten through eighth grade. The district operates multiple elementary schools and middle schools, including Edgewood and Northwood Middle Schools, ensuring localized and community-focused learning environments. District 112 is recognized for its commitment to academic excellence and innovation, offering a robust curriculum that includes dual-language programs and advanced STEM initiatives. With a focus on modernizing facilities and personalized instruction, the district consistently prepares students for high achievement. Graduates typically matriculate to Highland Park High School within Township High School District 113, continuing a tradition of superior educational performance.

5. Lake Forest

Renowned for its sprawling estates and an air of exclusivity, Lake Forest consistently ranks as one of the wealthiest Chicago suburbs.

Median Home Price 

The median home price in the Lake Forest area is about $1.1 million, but properties often exceed $7 million.

Why It’s Pricey 

• Historical Significance: This area is rich in history, featuring numerous mansions that date back to the 1800s. These architectural gems reflect the opulent past and add a unique charm, attracting those who appreciate classic architecture.
• Prestigious Education: Renowned institutions like Lake Forest Academy offer top-tier private education with a variety of extracurricular activities and advanced programs.
• Serene Lifestyle: The area is known for its rolling landscapes, lush greenery, and proximity to the lake, offering stunning views and a tranquil environment. Its scenic beauty provides ample opportunities for outdoor activities such as hiking, sailing, and relaxing in nature.

Lake Forest School District

Lake Forest School District 67 provides an exemplary public education for students in Lake Forest, Illinois. The district serves students from early childhood through eighth grade across four schools: Cherokee, Everett, and Sheridan elementary schools, and Deer Path Middle School. Renowned for its commitment to academic excellence and whole-child development, District 67 is consistently ranked among the best in the nation. It offers a rigorous curriculum focused on personalized instruction, inquiry-based learning, and innovation. The district’s strong financial health and community support enable it to provide state-of-the-art facilities and robust programming. Graduates matriculate to the highly-regarded Lake Forest High School, exceptionally well-prepared for future academic success.

6. Hinsdale

Hinsdale offers a blend of sophistication and small-town charm, making it a coveted suburb just outside the bustling streets of Chicago. Known for its historic landmarks and picturesque setting, it provides a high-end lifestyle coupled with community warmth.

Median Home Price

The median home price in Hinsdale is around $950,000, with select properties boasting price tags of $5 million or more, especially those with larger lots and unique architectural designs.

Why It’s Pricey 

• Scenic Beauty: The village is renowned for its lush parks, winding streets, and well-preserved architecture, offering a peaceful retreat from the city. The picturesque landscape is complemented by beautifully maintained gardens and tree-lined avenues.
• Top-Ranked Schools: Hinsdale Central High School is consistently recognized for academic excellence, offering a wide range of extracurricular activities and advanced placement courses.
• Community Vibe: The historic downtown area is filled with boutique shopping, dining options, and seasonal events. Frequent farmers’ markets, art fairs, and festive parades create a vibrant social life with plenty of opportunities to connect with others.

Hinsdale School District

Community Consolidated School District 181 serves students in Hinsdale and parts of Clarendon Hills and Burr Ridge, Illinois. This esteemed district provides education for students from kindergarten through eighth grade across seven elementary schools and two middle schools, including Hinsdale Middle School and Clarendon Hills Middle School. District 181 is nationally recognized for its exceptional academic performance and commitment to student growth. The district consistently achieves top rankings for its test scores and comprehensive curriculum, which emphasizes critical thinking and personalized learning. With a strong focus on preparing students for future success, District 181 provides a foundation of excellence. Graduates matriculate to the highly-rated Hinsdale Township High School District 86.

7. Burr Ridge

Burr Ridge is known for its spacious homes and lush landscapes, making it a desirable locale for those seeking tranquility and luxury just a short drive from Chicago. With its reputation for privacy and exclusivity, Burr Ridge attracts those who value both comfort and convenience.

Median Home Price 

The median home price in Burr Ridge is approximately $900,000, with many luxurious estates reaching up to $3 million or more.

Why It’s Pricey 

• Expansive Properties: Homes in this area are situated on large lots, offering ample space and a sense of privacy. The generous land plots allow for extensive gardens, outdoor entertainment areas, and potential for property expansions or renovations.
• Affluent Lifestyle: The community is known for its high-end shopping centers, gourmet dining establishments, and luxurious recreational facilities. Exclusive boutiques, top-rated restaurants, and private clubs provide a wide array of leisure options.
• Transportation Access: The suburb’s convenient location near major highways and public transport options ensures straightforward and efficient commuting. Whether traveling for work or leisure, reduced travel times and easy access to the city’s key areas add to the appeal.

Burr Ridge School District

The village of Burr Ridge, Illinois, is served by several highly-regarded public school districts, reflecting its commitment to quality education. The primary district is Burr Ridge School District 180, which operates the Burr Ridge Middle School and Anne M. Jeans Elementary School, serving students from pre-kindergarten through eighth grade. Portions of the village are also zoned for Community Consolidated School District 181 (Hinsdale) and Gower School District 62. These districts are known for their academic rigor, strong community involvement, and excellent student outcomes. Upon graduating, students from these districts typically matriculate to the acclaimed Hinsdale Township High School District 86, ensuring a continuous path of high-level education.

 

8. Western Springs

Western Springs is a quaint and charming suburb that offers a balance of suburban tranquility and modern convenience. Known for its historic charm and welcoming atmosphere, it’s located just outside Chicago.

Median Home Price

The median home price in Western Springs is around $750,000, with select custom homes fetching prices upwards of $1.5 million, especially in more desirable areas of the village.

Why It’s Pricey

• Community Spirit: Western Springs has a strong sense of community, with numerous local events and activities that foster connections and create a vibrant atmosphere.
• Architectural Character: The suburb features vintage homes with beautiful architectural designs, ranging from classic Victorian styles to mid-century modern masterpieces. This architectural diversity enhances its visual appeal and reflects the area’s rich history.
• Convenient Location: Strategically positioned near major expressways, Western Springs offers quick and easy access to downtown Chicago and surrounding areas. The well-connected Metra station further simplifies commuting and exploring the region.

Western Springs School District

Western Springs School District 101 serves the community of Western Springs, Illinois, providing high-quality public education for students from kindergarten through eighth grade. The district operates four distinct schools: Field Park, Forest Hills, and Laidlaw elementary schools, along with McClure Junior High School. District 101 is widely recognized for its academic excellence and student-centered approach. It consistently ranks among the top districts in the state, focusing on a rigorous curriculum that fosters critical thinking and social-emotional development. The district’s strong partnership with the community ensures a supportive learning environment. Graduates typically advance to Lyons Township High School District 204, well-prepared for future academic success.

9. Elmhurst 

Elmhurst strikes a perfect balance between suburban life and urban accessibility, making it a top choice for Chicago area home buyers looking outside the city. Known for its vibrant culture and strong community involvement, this suburb offers a dynamic living environment within commuting distance of downtown Chicago.

Median Home Price

The median home price in Elmhurst is approximately $525,000, with some luxury properties priced over $1 million, especially those with ample land and custom designs.

Why It’s Pricey

• Cultural Attractions: Elmhurst is home to the renowned Elmhurst Art Museum, which showcases contemporary art and offers various exhibitions throughout the year. The thriving downtown area is vibrant with a diverse range of shops, restaurants, and entertainment options, making it a cultural hub for both residents and visitors.
• Educational Opportunities: The suburb boasts excellent public schools, known for their high academic standards and comprehensive programs. Elmhurst University also contributes significantly to the area’s strong educational reputation, offering a variety of undergraduate and graduate programs that attract students from across the country.
• Convenient Amenities: Residents benefit from easy access to public transportation, including Metra trains that provide a quick commute to Chicago. Major highways such as I-290 and I-294 are nearby, ensuring seamless connectivity to Chicago and neighboring suburbs, making daily travel and commuting hassle-free.

Elmhurst School District

Elmhurst Community Unit School District 205 provides a comprehensive public education for students in Elmhurst, Illinois. Serving students from early childhood through grade 12, the district includes eight elementary schools, three middle schools, and the highly-regarded York Community High School. District 205 is distinguished by its commitment to academic excellence, innovative instruction, and strong community engagement. It has earned numerous state and national accolades for its student achievement, outstanding teachers, and robust academic and extracurricular programs. With a clear focus on preparing all students for post-secondary success, District 205 stands as a pillar of the Elmhurst community, known for its high standards and exceptional educational outcomes.

 

10. Wilmette

Wilmette combines lakeside beauty with suburban sophistication. Known for picturesque neighborhoods and rich architectural heritage, Wilmette offers an inviting atmosphere just north of Chicago.

Median Home Price

The median home price in Wilmette is approximately $650,000, with lakefront properties and historic homes reaching upwards of $2 million.

Why It’s Pricey

• Lakeside Charm: Proximity to Lake Michigan provides breathtaking views and access to stunning beaches and well-maintained parks, ideal for outdoor activities like swimming and leisurely strolls.
• Architectural Elegance: Renowned for its historic homes, including several on the National Register of Historic Places, Wilmette offers a unique blend of historical and aesthetic significance.
• Cultural and Educational Hub: Cultural attractions like the Wilmette Theatre and highly rated schools enhance the appeal, creating an enriching environment.
• Community Amenities: A vibrant downtown with diverse shops, restaurants, and cafes adds to the lively atmosphere. Excellent public transportation links ensure easy access to Chicago for commuters.

Wilmette School District

Wilmette Public Schools District 39 serves the majority of Wilmette, Illinois, offering a top-tier education for students from pre-kindergarten through eighth grade. The district is composed of six schools: four elementary schools (Central, Harper, McKenzie, and Romona), Highcrest Middle School for grades 5-6, and Wilmette Junior High School for grades 7-8. District 39 is consistently recognized as one of the premier public school districts in the state and nation. It is distinguished by its rigorous academic curriculum, comprehensive arts and technology programs, and a strong commitment to meeting the individual needs of every learner. Graduates matriculate to the highly acclaimed New Trier Township High School.

11. Lake Bluff

Lake Bluff is a serene lakeside suburb that offers picturesque landscapes and a peaceful retreat from city life. Located on the shores of Lake Michigan, this village balances natural beauty with a close-knit community vibe.

Median Home Price

The median home price in Lake Bluff is around $699,000, with waterfront properties and larger estates extending upwards of $3 million.

Why It’s Pricey

• Lakeside Living: Nestled along the shores of Lake Michigan, Lake Bluff offers stunning views, beautiful beaches, and outdoor activities like sailing, kayaking, and hiking along scenic trails.
• Community Engagement: Active local events such as farmer’s markets, art fairs, and community concerts create a vibrant, engaging atmosphere.
• Historical Charm: The suburb features a blend of historic homes, some dating back to the early 1900s, alongside modern architecture, offering a distinct character with rich historical appeal.
• Easy Access: Proximity to major highways and a direct Metra line to Chicago ensure convenient commutes and urban connectivity.

Lake Bluff School District

Lake Bluff School District 65 provides an exceptional education for students in the village of Lake Bluff, Illinois. Serving students from kindergarten through eighth grade, the district comprises two schools: Lake Bluff Elementary School for grades K-5 and Lake Bluff Middle School for grades 6-8. This structure fosters a close-knit and continuous learning environment. District 65 is renowned for its high academic standards, innovative teaching practices, and strong community support. It consistently earns recognition for outstanding student performance and its commitment to developing well-rounded individuals through a rich curriculum. Graduates matriculate to the acclaimed Lake Forest High School, exceptionally prepared for advanced academic challenges.

12. Naperville

Naperville is a dynamic suburb known for its vibrant downtown, excellent schools, and appealing atmosphere, making it one of the most desirable places to live in the Chicago metropolitan area. Often recognized for its high quality of life, the Village of Naperville offers a mix of suburban charm and urban amenities.

Median Home Price 

The median home price in Naperville is approximately $450,000, but properties can range significantly, with luxury homes exceeding $1 million, particularly in exclusive neighborhoods.

Why It’s Pricey 

• Top-Rated Schools: Naperville schools are consistently ranked among the best in Illinois, attracting individuals who prioritize education.
• Thriving Economy: The suburb boasts a robust local economy with diverse job opportunities, particularly in technology and healthcare sectors.
• Vibrant Downtown: With a picturesque Riverwalk, an array of shops, restaurants, and cultural venues, downtown Naperville serves as an attractive hub for residents and visitors.
• Community-Oriented: Known for its numerous events, including festivals and cultural gatherings, Naperville fosters a strong sense of engagement and pride.
• Transportation Options: Easy access to I-88 and a well-served Metra station make commuting to Chicago convenient, complementing Naperville’s appeal to professionals working in the city.

Naperville School District

Naperville is served by two nationally acclaimed school districts: Naperville Community Unit School District 203 and Indian Prairie School District 204. Both districts provide comprehensive education from early childhood through 12th grade and are consistently ranked among the best in the state and nation. District 203 includes Naperville Central and Naperville North High Schools, while District 204 operates Neuqua Valley, Metea Valley, and Waubonsie Valley High Schools. Renowned for their rigorous academics, exceptional test scores, and extensive extracurricular programs, these districts are a major draw for families, offering a premier public education that prepares students for top-tier universities.

13. River Forest

River Forest is a tranquil suburb that combines an upscale residential environment with the charm of lush greenery and historic architecture. Adjacent to the thriving Oak Park, River Forest offers a serene living experience while being conveniently close to the urban attractions of Chicago.

Median Home Price 

The median home price in River Forest is approximately $700,000, with larger estates and architecturally significant properties priced upwards of $1.5 million.

Why It’s Pricey 

• Architectural Distinction: Known for its Frank Lloyd Wright and Prairie School architecture, the suburb boasts a visually stunning collection of homes that attract architecture enthusiasts.
• Educational Excellence: With top-rated schools and proximity to Dominican University, River Forest is a favored choice for those who value educational quality.
• Natural Beauty: The suburb’s beautiful parks, including Cummings Square right in the heart of town, and tree-lined streets offer a peaceful retreat, enhancing the overall quality of life.
• Vibrant Community Life: River Forest hosts a range of events and recreational activities, fostering a close-knit, welcoming environment.
• Convenient Connectivity: Situated near major highways and public transportation, including the Metra and CTA Green Line in neighboring Oak Park, River Forest ensures easy access to Chicago and neighboring suburban areas while retaining its tranquility.

River Forest School District

River Forest Public Schools District 90 provides an exemplary education for students in River Forest, Illinois. The district serves children from kindergarten through eighth grade across three schools: Lincoln and Willard Elementary Schools and Roosevelt Middle School. This structure ensures a focused, community-oriented educational experience. District 90 is distinguished by its high academic achievement, progressive teaching methodologies, and a strong commitment to fostering an inclusive learning environment. The district consistently receives top ratings for its rigorous curriculum and dedicated faculty. Graduates are well-prepared for the next stage of their education, matriculating to the highly respected Oak Park and River Forest High School District 200.

14. Oak Brook

Oak Brook is an affluent suburb known for its lush estates, world-class amenities, and thriving business district. Situated just west of Chicago, it offers a blend of suburban tranquility and urban sophistication.

Median Home Price

The median home price in Oak Brook is approximately $800,000, with luxury properties and expansive estates reaching prices well over $3 million.

Why It’s Pricey

• Economic Hub: Oak Brook is home to a significant business center, attracting numerous corporate headquarters, which bolsters the local economy and contributes to the high demand for residences.
• Premier Shopping and Dining: The suburb boasts the renowned Oakbrook Center, one of the largest outdoor shopping malls in the country, featuring an array of upscale shops and fine dining options.
• Exclusive Lifestyle: Enjoy access to prestigious country clubs, golf courses, and upscale health and wellness centers, ensuring a luxurious lifestyle experience.
• Educational Opportunities: Known for high-quality public and private schools, as well as proximity to respected institutions like the College of DuPage.
• Connectivity: Convenient access to major highways like I-88 and I-294, as well as its strategic location near O’Hare and Midway airports, offers straightforward connectivity to both Chicago and national destinations.

Oak Brook School District

Oak Brook offers families access to exceptional public schools through two primary districts: Butler School District 53 and Community Consolidated School District 181. Butler District 53, located entirely within Oak Brook, serves students from early childhood to eighth grade at Butler Junior High and Brook Forest Elementary. It is consistently ranked among the top districts in Illinois for its outstanding academic performance and personalized instruction. Portions of Oak Brook are also served by District 181. Following eighth grade, students from both districts matriculate to the highly acclaimed Hinsdale Township High School District 86, specifically attending Hinsdale Central High School, ensuring a seamless, high-quality educational path.

15. Barrington

Barrington is a picturesque suburb located northwest of Chicago, known for its expansive plot sizes, elite equestrian culture, and charming downtown area. It exudes a quintessential small-town vibe while offering modern amenities and scenic landscapes.

Median Home Price

The median home price in Barrington is about $600,000, with large estates and equestrian properties frequently exceeding $2 million, making it one of the more upscale communities in the region.

Why It’s Pricey

• Equestrian Lifestyle: Barrington is renowned for its equestrian facilities and horse farms, attracting enthusiasts who seek a rural lifestyle combined with suburban convenience.
• Charming Downtown: The vibrant downtown area features unique shops, fine dining, and regular community events, enhancing the small-town charm.
• Top Schools: Offers highly-rated public and private schools, adding to its appeal.
• Natural Surroundings: With access to numerous parks, forest preserves, and lakes, Barrington provides endless outdoor recreational opportunities, promoting a healthy and active lifestyle.
• Accessibility: Offers a peaceful rural environment while being well-connected through major highways and a Metra line to downtown Chicago, making it suitable for commuters.

Barrington School District

Barrington Community Unit School District 220 serves a large area encompassing Barrington and surrounding communities. This comprehensive district provides education for students from early childhood through 12th grade. It includes eight elementary schools, two middle school campuses for grades 6-8, and the nationally recognized Barrington High School. District 220 is celebrated for its commitment to academic excellence and innovative programming, including unique options like a Mandarin Chinese immersion program. Known for its rigorous curriculum, high student achievement, and extensive extracurricular opportunities, the district focuses on personalized learning and future readiness, making it a cornerstone of the community and a draw for families.

16. South Barrington

South Barrington is a prestigious enclave northwest of Chicago, admired for its luxurious estates, exclusive lifestyle, and serene suburban atmosphere.

Median Home Price

The median home price in South Barrington is approximately $950,000, with many luxury homes and expansive properties exceeding $3 million, making it one of the most upscale communities in the Chicagoland area.

Why It’s Pricey

• Luxurious Estates: South Barrington offers vast properties with custom-built homes that emphasize grandeur and seclusion.
• The Arboretum of South Barrington: This premier shopping and dining destination features upscale retailers, eateries, and entertainment options.
• Community Amenities: The village includes private clubs, golf courses, and fitness centers, enhancing the luxurious lifestyle.
• Proximity to Nature: Forest preserves and scenic trails provide natural beauty and recreational opportunities for a balanced and healthy lifestyle.
• Convenient Location: Located near major highways, South Barrington offers easy access to Chicago and other suburban areas while maintaining its peaceful charm.

South Barrington School District

South Barrington is primarily served by the esteemed Barrington Community Unit School District 220, a district renowned for its high standards and comprehensive educational offerings. District 220 provides a complete K-12 academic journey, encompassing several elementary schools, two middle school campuses, and the nationally ranked Barrington High School.

Families in South Barrington benefit from the district’s commitment to academic excellence, evidenced by consistently high student achievement and innovative programs. With a focus on personalized learning and preparing students for post-secondary success, District 220 offers a rigorous curriculum, diverse extracurriculars, and unique learning pathways, making it a key asset for the community.

17. Oak Park

Oak Park is a vibrant suburb adjacent to the west side of Chicago, celebrated for its rich architectural heritage, cultural attractions, and dynamic living environment.

Median Home Price

The median home price in Oak Park is approximately $400,000, with historic and architecturally significant properties often exceeding $1 million.

Why It’s Pricey

• Architectural Significance: Oak Park is home to numerous Frank Lloyd Wright-designed buildings and other historic residences, drawing architecture enthusiasts worldwide.
• Cultural Vibrancy: The suburb features a thriving arts scene with galleries, theaters, and festivals, creating a lively atmosphere.
• Diverse Amenities: From unique shops and gourmet restaurants to lush parks and recreational facilities, Oak Park offers a dynamic and enriching lifestyle.
• Excellent Connectivity: With direct access to downtown Chicago via the CTA Green Line and Metra trains, Oak Park provides urban convenience with suburban charm.

Oak Park School District

Oak Park is served by two distinguished public school districts. Oak Park Elementary School District 97 provides education for students from kindergarten through eighth grade. The district comprises eight elementary schools and two middle schools, all focused on fostering an equitable and inclusive learning environment. District 97 is recognized for its progressive curriculum and commitment to academic excellence for every student. Upon completion of middle school, students advance to Oak Park and River Forest High School District 200. The high school is renowned for its rigorous academic programs, extensive arts and athletic offerings, and a long history of student achievement and national recognition.

18. Glenview

The Village of Glenview is a well-respected northern suburb of Chicago, known for its picturesque neighborhoods, strong community values, and excellent public services.

Median Home Price 

The median home price in Glenview is around $500,000, with a variety of housing options, from charming single-family homes to luxurious estates exceeding $1.5 million.

Why It’s Pricey 

• Community Focused: Glenview is known for its vibrant community atmosphere, with festivals, events, and programs that foster a sense of belonging.
• The Glen Town Center: This shopping and entertainment district combines retail stores, dining options, and cultural venues, enhancing the local lifestyle.
• Parks and Recreation: The area offers numerous parks, golf courses, and outdoor facilities, supporting an active and healthy lifestyle.
• Cultural and Historic Charm: As the home of the historic Grove National Historic Landmark and a thriving Arts Center, Glenview appeals to those interested in culture and history.
• Transportation and Accessibility: With access to major highways and the Metra commuter rail, Glenview provides seamless connectivity to Chicago and surrounding areas.

Glenview School District

The village of Glenview is served by several highly-regarded public school districts, providing a comprehensive educational experience. For students in pre-kindergarten through eighth grade, Glenview School District 34 is the primary district. It includes multiple elementary schools and two middle schools, Attea and Springman, and is known for its strong academic foundation and focus on student growth. Upon graduating, students matriculate to Glenbrook High School District 225, a premier district nationally recognized for excellence. Most Glenview students attend Glenbrook South High School, which is celebrated for its rigorous academic programs, extensive Advanced Placement offerings, award-winning fine arts, and competitive athletics. Together, these districts maintain a reputation for academic distinction.

19. Park Ridge

Park Ridge is located 14 miles northwest of downtown Chicago. Known for its picturesque streets and historic homes, this suburb blends urban convenience with suburban tranquility.

Median Home Price 

The median home price in Park Ridge is approximately $575,000, with historic homes and modern residences that can exceed $1 million.

Why It’s Pricey 

• Historic Character: Well-maintained historic homes and buildings contribute to Park Ridge’s classic charm and high property values.
• Cultural Attractions: Highlights include the Pickwick Theatre and the Iannelli Studios Heritage Center, appealing to those passionate about arts and culture.
• Community-Oriented Lifestyle: Events like farmers’ markets and festivals foster a welcoming atmosphere.
• Green Spaces: With abundant parks and recreational facilities, Park Ridge supports an active lifestyle.
• Transportation Access: Its proximity to O’Hare International Airport, major highways, and the Metra train service ensures excellent connectivity to the city and beyond.

Park Ridge School District

Park Ridge, Illinois, is served by two distinguished educational systems: Park Ridge-Niles School District 64 and Maine Township High School District 207. District 64 provides a robust K-8 education across five elementary schools, two middle schools (Emerson and Lincoln), and an early childhood center. It is recognized for its focus on comprehensive student development and modernized curriculum. Upon graduation, students typically transition to Maine South High School within District 207. Maine South is consistently ranked among the top high schools in the state and nation, renowned for its rigorous Advanced Placement offerings, exceptional fine arts programs, and competitive athletics. Together, these districts uphold a strong reputation for scholastic excellence.

20. Evanston

Evanston is a diverse and vibrant suburb north of Chicago, known for its cultural scene, prestigious educational institutions, and a mix of urban and suburban lifestyles.

Median Home Price 

The median home price in Evanston is approximately $450,000, with options ranging from older homes to modern luxury apartments.

Why It’s Pricey 

• Proximity to Lake Michigan: Evanston features lakefront properties and scenic beaches, attracting those who value waterfront living.
• Academic Prestige: As the home of Northwestern University, Evanston is a hub for students, academics, and professionals, influencing its community and economy.
• Cultural Richness: The area is filled with theaters, galleries, music venues, and a variety of festivals and community events.
• Diverse Neighborhoods: Evanston offers unique neighborhoods catering to various lifestyles and preferences.
• Green Spaces and Parks: The suburb provides ample parks and outdoor facilities for recreation and leisure.
• Transportation Convenience: Evanston’s location along the CTA Purple Line and Metra ensures easy access to Chicago, offering urban accessibility with suburban benefits.

Evanston School District

Evanston is served by two highly regarded public school districts that provide a continuous educational path from early childhood through high school. Evanston/Skokie School District 65 serves students from pre-kindergarten to eighth grade. It includes numerous elementary and middle schools known for their commitment to equity, diverse learning programs, and strong community involvement. Upon completing middle school, students matriculate to Evanston Township High School (ETHS) District 202. ETHS is a comprehensive high school celebrated for its academic rigor, extensive Advanced Placement courses, award-winning arts and athletics, and a wide array of career and technical education pathways.