These 5 Cities Has the Most Expensive Homes in Illinois

Illinois, known for its vibrant cities, sprawling farmlands, and rich history, offers a wide range of housing options. However, some cities within the Land of Lincoln stand out for their exceptionally high real estate prices. This article delves into the top 5 Illinois cities boasting the most expensive homes, exploring the unique qualities and dynamics that shape these exclusive markets.

1. Kenilworth: The Crown Jewel of the North Shore

  • Median Home Value: $1,500,000+ (approx.)
  • Factors Contributing to High Prices:
    • Historical Affluence: Founded in the late 19th century as a planned community for Chicago’s elite, Kenilworth has maintained its reputation for wealth and exclusivity.
    • Lakefront Location: Many homes enjoy stunning views of Lake Michigan and direct beach access.
    • Chicago Proximity: A short commute to downtown Chicago makes it desirable for high-income professionals.
    • Architectural Significance: Kenilworth showcases works by renowned architects like Howard Van Doren Shaw and David Adler.

2. Winnetka: Picturesque Lakeside Living

  • Median Home Value: $1,400,000+ (approx.)
  • Factors Contributing to High Prices:
    • Nationally Ranked Schools: Winnetka’s public schools consistently rank among the best in Illinois and the nation.
    • Village Charm: Tree-lined streets, quaint downtown, and proximity to the lake create a sought-after ambiance.
    • Diverse Housing: A mix of historic homes, grand estates, and contemporary builds offer options for various luxury buyers.

3. Glencoe: A Haven of Elegance

  • Median Home Value: $1,300,000+ (approx.)
  • Factors Contributing to High Prices:
    • Tranquility and Exclusivity: Glencoe offers a peaceful retreat while maintaining easy access to Chicago and lakefront amenities.
    • Excellent School System: Glencoe schools are known for strong academics and a nurturing environment.
    • Natural Beauty: The village features ravines, parks, and Lake Michigan shoreline.

4. Hinsdale: Suburban Sophistication

  • Median Home Value: $1,000,000+ (approx.)
  • Factors Contributing to High Prices:
    • Commuting Convenience: Hinsdale offers a desirable mix of suburban living and proximity to Chicago’s central business district.
    • Variety of Upscale Housing: From historic estates to modern luxury homes, Hinsdale caters to diverse tastes.
    • Strong School Reputation: Hinsdale’s schools attract families seeking exceptional educational opportunities.

5. Lake Forest: A Legacy of Grandeur

  • Median Home Value: $900,000+ (approx.)
  • Factors Contributing to High Prices:
    • Historic Mansions and Estates: Lake Forest boasts an array of architecturally significant homes dating back to the early 20th century.
    • Prestigious Institutions: Home to Lake Forest College and top-ranked private schools.
    • Natural Amenities: Expansive grounds, proximity to Lake Michigan, and access to parks and nature preserves.

Factors Driving High Housing Costs across Illinois’s Most Expensive Cities

  • Strong Local Economies: These affluent communities boast thriving industries and attract high-income earners seeking a luxurious lifestyle close to their places of work.
  • Limited Housing Supply: A combination of factors like zoning regulations, land availability, and the desire to maintain exclusivity constrain the supply of new homes, driving prices upwards.
  • Demand from High-Net-Worth Individuals: These cities are desirable to affluent families, executives, and retirees seeking spacious properties, top-notch amenities, and access to the best the region offers.
  • Investment Value: Homes in these areas tend to hold their value well over time and are even treated as appreciating assets within investment portfolios.

The Luxurious Lifestyle

Living in Illinois’s most expensive cities comes with a unique set of benefits and a quality of life that sets them apart:

  • Beautiful Surroundings: From meticulously landscaped estates and historic mansions to pristine beaches and vibrant downtowns, these towns offer a visually stunning environment.
  • Prestigious Schools: These communities prioritize education, leading to some of the highest-rated public and private schools in the state, attracting families who value academic excellence.
  • Exclusive Amenities: Residents often have access to top-tier golf courses, country clubs, private beaches, and yacht clubs, offering opportunities for recreation and social connection.
  • Cultural Access: These affluent suburbs are often near world-class museums, theaters, and cultural events in Chicago.

Important Considerations

Of course, choosing to reside in one of these cities also involves certain tradeoffs:

  • High Property Taxes: Residents of these exclusive areas typically pay significantly higher property taxes to support excellent schools and services.
  • Cost of Living: The overall cost of living, from groceries to dining and entertainment, tends to be elevated compared to other areas in Illinois.
  • Potential for Social Exclusivity: Some of these communities may be perceived as less diverse or inclusive in terms of socioeconomic backgrounds.



Illinois’s most expensive cities offer a blend of luxury, natural beauty, educational excellence, and proximity to the dynamic metropolis of Chicago. While the cost of entry may be high, these communities provide a unique and highly desirable lifestyle for those who prioritize exclusivity, prestige, and the finer things in life.

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MBS Staff
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