Illinois is home to some of the most expensive cities in the country, offering luxurious homes, upscale amenities, and premier neighborhoods. Whether you’re looking at homes for sale in Winnetka or Long Grove, these cities deliver elegance and comfort. While these locations offer incredible living experiences, they come with a premium price tag. If you’re not ready for the investment, exploring other nearby options might be a better fit for your budget. Here’s Redfin’s list of the most expensive cities in Illinois.
Quick facts about Illinois
| Median sale price | $283,200 |
| Median household income | $80,306 |
| Average rent | $2,223 |
10. Western Springs, IL
Median Sale Price: $936,000
Homes for Sale in Western Springs
Western Springs is known for its charming downtown and tree-lined streets that create a peaceful yet upscale vibe. The Historic Water Tower stands as a local landmark, representing the town’s rich heritage. Residents enjoy boutique shopping, local restaurants, and easy access to nearby forest preserves. The neighborhood boasts a mix of historic and modern luxury homes. Its proximity to downtown Chicago makes it attractive for those seeking suburban luxury without feeling disconnected from the big city.
9. Long Grove, IL
Median Sale Price: $967,500
Homes for Sale in Long Grove
Rustic charm and preserved historic district make Long Grove a unique and desirable place to live. The covered bridge, an iconic local attraction, enhances the area’s small-town feel. Residents can explore locally owned shops, art galleries, and outdoor concerts in the town center. Spacious estates and custom homes are nestled among nature, offering privacy and scenic views. Long Grove combines luxury living with countryside charm, making it a top choice for homebuyers.
8. Bannockburn, IL
Median Sale Price: $1,000,000
Homes for Sale in Bannockburn
Bannockburn is an exclusive community known for its sprawling estates and secluded atmosphere. The village is surrounded by natural beauty, with trails and parks perfect for outdoor enthusiasts. Bannockburn’s upscale homes often feature large lots, elegant architecture, and modern designs. Despite its tranquil surroundings, it offers convenient access to shopping centers and major highways.
7. Wilmette, IL
Median Sale Price: $1,100,000
Homes for Sale in Wilmette
Wilmette offers lakeside living with stunning views of Lake Michigan and plenty of recreational opportunities. Gillson Park, a local favorite, features beaches, boating, and trails. The town’s lively downtown boasts high-end dining, unique shops, and cultural venues like the Wilmette Theatre. The area is known for its historic homes, lakefront mansions, and modern builds, offering something for all luxury seekers. Its proximity to Chicago makes it ideal for those who crave both comfort and convenience.
6. Kildeer, IL
Median Sale Price: $1,160,000
Homes for Sale in Kildeer
Blending luxury with nature, Kildeer offers expansive homes surrounded by wooded landscapes and rolling hills. The Deer Park Town Center nearby provides access to upscale shopping and dining. Residents can enjoy outdoor activities at nearby nature preserves or private golf courses. Kildeer’s spacious estates are designed to provide privacy and elegance. Homebuyers seeking tranquility without sacrificing proximity to urban amenities will find Kildeer appealing.
5. Glencoe, IL
Median Sale Price: $1,165,000
Homes for Sale in Glencoe
Glencoe is a lakeside gem, known for its pristine beaches and proximity to the Chicago Botanic Garden. The Ravinia Festival, a major attraction, hosts world-class music performances each summer. The village’s downtown area features boutique shops, gourmet eateries, and charming cafés. Glencoe’s luxury homes, ranging from historic estates to contemporary builds, attract those seeking elegance and exclusivity.
4. South Barrington, IL
Median Sale Price: $1,250,000
Homes for Sale in South Barrington
South Barrington offers grand homes with sprawling lawns, private gated communities, and upscale amenities. The Arboretum of South Barrington, a high-end shopping and entertainment complex, serves as a local hotspot. Residents can also enjoy recreational activities at nearby nature reserves and country clubs. Its luxurious atmosphere and access to leisure activities make it highly desirable.
3. Barrington Hills, IL
Median Sale Price: $1,635,850
Homes for Sale in Barrington Hills
Barrington Hills is known for its spacious properties, large estates, and private settings. The community is surrounded by scenic countryside, with miles of riding trails and open spaces. Homes here often sit on large lots, offering seclusion and elegance. Residents can enjoy outdoor recreation at the Spring Creek Forest Preserve and other nearby parks. Its blend of rural charm and upscale living attracts those seeking a peaceful yet luxurious lifestyle.
2. North Barrington, IL
Median Sale Price: $1,700,000
Homes for Sale in North Barrington
If you’r in the market for luxury, exclusive gated communities and expansive estates, look no further than North Barrington. Golf enthusiasts enjoy access to the Wynstone Golf Club, a private club known for its picturesque course. The area is filled with custom homes featuring high-end finishes and lavish designs. North Barrington provides a serene escape while remaining close to shopping, dining, and recreational activities. Its prestige and privacy make it a top contender for luxury homebuyers.
1. Winnetka, IL
Median Sale Price: $2,175,000
Homes for Sale in Winnetka
Winnetka stands out as the most expensive city in Illinois, offering opulent homes and an upscale lifestyle along Lake Michigan’s shores. The village’s picturesque landscapes include parks, beaches, and scenic walking trails. The Hubbard Woods business district provides access to high-end boutiques and dining options. Residents enjoy a blend of historic mansions and modern luxury homes.
What are the richest cities in Illinois?
Based on median household income, the richest cities in Illinois are:
| City | Median household income |
| Winnetka, IL | $250,001 |
| Riverwoods, IL | $231,477 |
| Kildeer, IL | $212,500 |
| Long Grove, IL | $207,188 |
| Hawthorn Woods, IL | $206,875 |
Where are the cheapest places to live in Illinois?
Not every city in Illinois comes with a high price tag. If you’re looking for affordable home prices and lower living costs, these cities offer budget-friendly options:
| City | Median home sale price |
| East St. Louis, IL | $45,000 |
| Sterling, IL | $48,000 |
| Cahokia, IL | $95,000 |
| Decatur, IL | $115,000 |
| Pekin, IL | $118,500 |
Methodology: Rankings based on median home sale price data sourced from Redfin.com during January 2025. Median household income sourced from U.S. Census Data.