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.

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.

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.

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.

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 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.

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.

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.

 

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.

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.

 

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.

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 $600,000, 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.

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.

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.

 

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.

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.

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.

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.

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.

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 $480,000, 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.

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.