Where Do Chicagoland’s Ultra-Wealthy Live?
A Look at the Most Expensive Zip Codes in the Chicago Suburbs
If you’ve ever wondered where the wealthiest families in Chicagoland live, you’re not alone. Chicago’s suburbs are home to some of the most prestigious communities in the Midwest—places defined not just by price tags, but by lifestyle, legacy, and long-term value.
In this guide, we break down seven of the wealthiest suburbs in Chicagoland, including three North Shore communities and four western suburbs, highlighting average prices, record sales, and what makes each location truly special.
The North Shore: Lakefront Luxury & Timeless Prestige
1. Winnetka
Often considered the crown jewel of the North Shore, Winnetka sits along Lake Michigan and is known for its iconic lakefront estates, historic architecture, and top-rated schools.
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Average asking price: ~$2.3M
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Average sold price: ~$1.68M
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Highest sale ever: $35M lakefront estate (2025)
Winnetka blends sophistication with small-town charm, making it one of the most desirable—and valuable—communities in Illinois.
2. Kenilworth
Kenilworth may be small in size, but it is massive in prestige. It consistently ranks as the town with the highest net income in Illinois.
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Average asking price: ~$3.3M
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Average sold price: ~$1.95M
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Highest sale: $14.5M lakefront mansion
With quiet streets, architectural perfection, and lake views, Kenilworth is one of the most exclusive enclaves in the state.
3. Wilmette
Wilmette offers a balanced blend of luxury and livability, making it especially attractive to families.
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Average asking price: ~$1.1M
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Average sold price: ~$1.07M
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Highest sale: $9M
Residents enjoy excellent schools, a walkable downtown, and classic North Shore living—often at a more accessible price point than Winnetka or Kenilworth.
The Western Suburbs: Space, Privacy & Suburban Sophistication
4. Hinsdale
Hinsdale defines western suburban luxury with stately homes, tree-lined streets, and a vibrant downtown.
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Average asking price: ~$1.3M
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Average sold price: ~$1.6M
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Highest public sale: ~$7.65M
Its charm, amenities, and proximity to Chicago continue to attract high-net-worth buyers.
5. Oak Brook
Known for corporate headquarters, luxury shopping, golf courses, and expansive lots, Oak Brook blends suburban calm with a cosmopolitan feel.
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Average asking price: ~$837K
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Average sold price: ~$1.6M
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Notable sales: Multiple $5M+ properties, including a $5.3M sale in 2025
Oak Brook remains a top choice for executives and luxury buyers seeking convenience and space.
6. Burr Ridge
Burr Ridge is ideal for buyers seeking privacy without sacrificing access.
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Average asking price: ~$1.4M
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Average sold price: ~$965K
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Highest sale: $6.9M
Gated estates, nature preserves, and a strong sense of community define this refined western suburb.
7. Western Springs
Rounding out the list is Western Springs, known for safety, schools, and family-friendly living.
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Average asking price: ~$989K
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Average sold price: ~$972,500
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Highest sale: $3.1M
Located just 25 minutes from downtown Chicago, it offers long-term value in a classic suburban setting.
Why These Communities Matter
These suburbs aren’t just about square footage—they’re about lifestyle, stability, and legacy.
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For buyers: Strong resale value, top-tier schools, and established neighborhoods
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For sellers: Serious, well-qualified buyers who value craftsmanship and location
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For investors: Understanding asking price vs. sold price vs. record sales leads to smarter long-term decisions
Whether you’re drawn to lakefront estates or western suburb sophistication, these communities represent the very best of Chicagoland living.
Thinking About Moving or Selling?
If you’d like a personalized breakdown of any of these suburbs—or want to know what your home is worth today—I’d be happy to help guide you.
Talk soon—and remember: Prove Them Wrong.