Illinois’s 14 Most Luxurious Suburbs With A Chicago-Area City On Top

Nestled around the bustling city of Chicago, Illinois boasts some of the most exclusive and upscale suburban communities in America. These prestigious neighborhoods offer stunning homes, top-rated schools, and amenities that define luxury living.

From historic mansions along Lake Michigan to modern estates with impeccable landscaping, these suburbs represent the pinnacle of sophisticated living in the Prairie State.

1. Kenilworth: The Crown Jewel Of North Shore

Meticulously planned from its inception in 1889, Kenilworth stands as the wealthiest suburb in Illinois. The community’s stunning lakefront estates often exceed $5 million, with tree-lined streets showcasing architectural masterpieces.

Residents enjoy an intimate village atmosphere where privacy and exclusivity reign supreme. With just about 2,500 residents, this tiny enclave maintains its reputation through strict zoning laws that preserve its elegant character.

2. Winnetka: Timeless Elegance By The Lake

Featured in classic films like “Home Alone,” Winnetka’s grand homes tell stories of old-world craftsmanship and multigenerational wealth. The village blends historic charm with modern luxury across its diverse neighborhoods.

Hubbard Woods and Indian Hill offer distinct personalities within this prestigious community. Downtown Winnetka delights with boutique shopping and gourmet dining options, while residents cherish access to private beaches and sailing clubs along Lake Michigan’s shores.

3. Glencoe: Where Nature Meets Luxury

Bordered by ravines and bluffs, Glencoe offers dramatic natural beauty alongside architectural splendor. The community treasures its connection to nature through the Chicago Botanic Garden and the Skokie Lagoons.

Modern mansions mingle with mid-century masterpieces throughout this diverse community. Residents enjoy private beach access, excellent schools, and a walkable downtown filled with upscale amenities while maintaining a relaxed, family-friendly atmosphere despite the area’s significant wealth.

4. Lake Forest: Historic Grandeur And Country Club Living

Founded as a retreat for Chicago’s elite, Lake Forest showcases some of the region’s most spectacular estate properties. Sprawling mansions sit on multi-acre lots, many designed by renowned architects like David Adler and Howard Van Doren Shaw.

The historic Market Square, America’s first planned shopping center, anchors this community with European-inspired charm. Prestigious institutions like Lake Forest College and the Onwentsia Club reinforce the town’s long-standing reputation as a bastion of old money and refined taste.

5. Hinsdale: Western Suburb Sophistication

Breaking away from the North Shore dominance, Hinsdale brings luxury living to Chicago’s western corridor. The village’s central location offers convenient access to downtown Chicago while maintaining a distinct small-town atmosphere.

Brick-paved streets in the downtown district lead to charming boutiques and acclaimed restaurants. Architectural diversity shines through the mix of historic homes and newer custom-built estates, with properties in the southeast section commanding some of the highest prices in the entire Chicago region.

6. Wilmette: Balanced Luxury With Community Spirit

Home to the stunning Bahá’í Temple, Wilmette offers architectural diversity ranging from historic lakefront mansions to charming Craftsman homes. The community balances luxury with approachability, creating an atmosphere that’s both exclusive and welcoming.

Plaza del Lago shopping center provides upscale retail experiences alongside neighborhood shops. Excellent public schools, beautiful beaches, and extensive park systems make Wilmette particularly attractive to affluent families seeking a balanced lifestyle with proximity to Chicago.

7. Deerfield: Modern Luxury With Corporate Connections

Serving as headquarters for major corporations like Walgreens and Caterpillar, Deerfield blends residential luxury with business prestige. The village’s newer luxury developments feature contemporary designs and smart-home technology.

Excellent schools consistently rank among Illinois’ best, attracting executives and professionals. The community offers a perfect balance of suburban tranquility and urban convenience, with upscale shopping at Deerfield Square and easy access to Chicago via the Metra or expressways.

8. Oak Brook: Shopping Paradise With Estate Living

Famous for its world-class shopping at Oakbrook Center, this western suburb combines retail luxury with residential opulence. The community grew around the prestigious Oak Brook Golf Club and the Butler family estate, establishing exclusivity from its beginnings.

Expansive lots feature custom-built mansions often exceeding 10,000 square feet. Corporate headquarters like McDonald’s (until recently) contributed to the area’s prosperity, while the absence of a village property tax adds financial appeal for wealthy residents seeking tax advantages alongside luxury living.

9. Barrington: Rural Luxury With Equestrian Flair

Stretching across multiple counties, Barrington encompasses several distinct communities united by a commitment to preserving open spaces. The area’s equestrian heritage remains strong, with many properties featuring horse facilities and access to riding trails.

Downtown Barrington charms with its historic buildings housing upscale boutiques and restaurants. Larger estates often include private ponds, rolling hills, and extensive woodlands, creating a countryside atmosphere despite being within commuting distance of Chicago.

10. Northbrook: Tech-Forward Luxury With Green Spaces

Northbrook balances modern luxury with environmental consciousness through its extensive park system and forest preserves. The village attracts tech executives and entrepreneurs with contemporary homes featuring smart technology and sustainable design elements.

Northbrook Court mall provides high-end shopping experiences close to home. Award-winning schools and recreational facilities like the Ed Rudolph Velodrome cycling track offer exceptional amenities for families, while corporate headquarters bring professional opportunities within the community itself.

11. Highland Park: Creative Luxury With Architectural Significance

Known for architectural treasures like multiple Frank Lloyd Wright homes and the iconic Mies van der Rohe-designed Farnsworth House, Highland Park celebrates creative luxury. The community embraces arts and culture through Ravinia Festival, North America’s oldest outdoor music venue.

Lakefront mansions command premium prices, while inland neighborhoods offer diverse architectural styles. The vibrant downtown area features independent boutiques, art galleries, and gourmet restaurants, creating a sophisticated atmosphere that attracts affluent professionals seeking cultural richness alongside luxury living.

12. Barrington Hills: Ultra-Exclusive Rural Estates

With a five-acre minimum lot requirement, Barrington Hills represents the ultimate in privacy and space among Chicago’s luxury suburbs. The community fiercely protects its rural character through strict zoning laws that prevent overdevelopment.

Equestrian culture thrives with private stables and miles of riding trails connecting properties. Estate homes often feature custom designs with amenities like indoor riding arenas, private lakes, and helicopter pads, creating self-contained compounds for residents seeking both luxury and seclusion.

13. Lake Bluff: Coastal Charm With Architectural Heritage

Originally developed as a lakefront resort community, Lake Bluff retains its vacation-like atmosphere with stunning Lake Michigan views. The village’s historic district showcases well-preserved examples of Victorian and Prairie School architecture.

Bluff’s Edge offers some of the most coveted properties, with homes perched dramatically above Lake Michigan. Community traditions like the Fourth of July parade and the Shakespeare Festival foster strong social connections, creating a tight-knit environment despite the area’s significant wealth and exclusivity.

14. Western Springs: Family-Focused Luxury With Historic Roots

Named for its natural springs, this western suburb combines historic charm with family-oriented luxury. The community’s signature Victorian homes and Tudors sit alongside newer custom-built residences on tree-lined streets.

The pedestrian-friendly downtown centers around the historic water tower and Metra station. Excellent schools and extensive recreational facilities attract affluent families, while the village’s dry status (prohibiting bars) maintains a traditional atmosphere that appeals to residents seeking both luxury and wholesome community values.