
Grand lakefront estates and tree-lined streets near Sheridan Road give Winnetka its North Shore luxury appeal. Residents enjoy access to private Lake Michigan beaches, exclusive clubs such as Winnetka Golf Club, and a charming dow...
Personal Safety : 98
Property Safety : 90
Community Safety : 89
$1,720,000
Median Home Rent
$1,995

Located in DuPage County, Hinsdale's prestigious 60521 ZIP code is among the richest in Illinois, with household incomes far exceeding state averages. The village is known for its stately homes, tree-lined streets, and nationally ...
Personal Safety : 93
Property Safety : 78
Community Safety : 79
$1,727,000
Median Home Rent
$3,800

The city is home to sprawling lakefront estates, gated properties, and grand residences set along the shores of Lake Michigan. Prestigious neighborhoods such as Onwentsia and Conway Farms attract affluent buyers seeking privacy, l...
Personal Safety : 95
Property Safety : 72
Community Safety : 90
$1,285,000
Median Home Rent
$4,300

Barrington Hills ranks among the wealthiest and most exclusive communities in Illinois. Known for its expansive estates, private equestrian properties, and custom-built homes on multi-acre lots, the village offers a level of priva...
Personal Safety : 91
Property Safety : 89
Community Safety : 81
$1,200,000
Median Home Rent
$3,800

Highland Park ranks among the most affluent and desirable communities on Illinois’ North Shore. Known for its beautiful lakefront setting, upscale neighborhoods, and strong sense of community, the city attracts executives, profess...
Personal Safety : 91
Property Safety : 78
Community Safety : 78
$763,000
Median Home Rent
$2,395

Oak Brook stands among the most exclusive and affluent suburbs in Illinois, combining luxury living with a strong business presence. The village is home to Oakbrook Center, one of the region’s premier shopping destinations, featur...
Personal Safety : 78
Property Safety : 39
Community Safety : 66
$1,050,000
Median Home Rent
$4,650

Western Springs is known for its charming historic character, tree-lined neighborhoods, and upscale homes. Luxury properties throughout the village, particularly near Old Town North and Spring Rock Park, attract buyers seeking bot...
Personal Safety : 97
Property Safety : 91
Community Safety : 92
$1,315,000
Median Home Rent
$4,150

Luxury, privacy, and small-town charm define Long Grove, one of the most expensive places to live in Illinois. Known for its spacious estates, wooded landscapes, and scenic setting, the village offers an exclusive residential atmo...
Personal Safety : 81
Property Safety : 83
Community Safety : 76
$830,000
Median Home Rent
$5,600

Lakefront luxury defines Wilmette. This North Shore suburb ranks among the most expensive places to live near Chicago. Elegant estates surround Lake Michigan, Gillson Park, and the private Wilmette Harbor marina. Wealthy families ...
Personal Safety : 90
Property Safety : 73
Community Safety : 84
$950,000
Median Home Rent
$3,900

Burr Ridge ranks among the most expensive places to live in Illinois. The village's gated communities, custom estates, and private wooded lots draw executives and business owners after a luxury lifestyle with quick access to downt...
Personal Safety : 76
Property Safety : 75
Community Safety : 80
$737,500
Median Home Rent
$2,400
High home prices are only part of the equation in Illinois's priciest markets. Groceries, utilities, and insurance all run above the national average. Here is what to expect across five of Illinois's most expensive cities.
| City | Median Home Price | Median Rent | Cost of Living | Rank |
|---|---|---|---|---|
| Winnetka | $1,720,000 | $1,995 | 1/10 | |
| Hinsdale | $1,727,000 | $3,800 | 2/10 | |
| Lake Forest | $1,285,000 | $4,300 | 3/10 | |
| Barrington Hills | $1,200,000 | $3,800 | 4/10 | |
| Highland Park | $763,000 | $2,395 | 5/10 |
Illinois gets a bad reputation sometimes, but the full picture tells a different story. Several cities across the state report violent and property crime rates well below the state average, based on the latest FBI crime data. Take a look at our safest places to live in Illinois rankings to see which cities made the list.
To determine the most expensive places to live, we applied a structured, data-driven methodology using verified economic and housing datasets. Our analysis incorporates employment levels and job stability (Bureau of Labor Statistics), cost of living benchmarks (C2ER), median home prices and average rents (Houzeo housing data), and income statistics from the U.S. Census Bureau. Each factor was normalized against its respective state average to control for regional cost differences and market size. The combined metrics were then weighted and aggregated to produce a final comparative score, highlighting cities where housing costs, cost of living, and overall expenses are strongest relative to the state and national baseline.
Transparent & data-driven
Each city is scored across five weighted categories using daily MLS data and verified government stats. Every metric is benchmarked against both its state average and the national average — dual benchmarking — so a market isn’t judged expensive just for sitting in a high-cost state.
Sale price, price per sq ft & high-value concentration vs. state and national benchmarks.
Median rent, rent-to-income ratio & rental demand vs. state and national medians.
The gap between median household income and the cost of living for the area.
Turnover, scarcity, days on market & buyer competition from Houzeo’s live MLS feed.
Utilities, transportation & everyday goods vs. state and national averages — the tiebreaker.
MLS metrics update daily; government data is added on each agency’s release schedule.
Important Legal Disclosures
MLS Disclaimers
The market analysis provided on this page is for informational purposes only and does not constitute financial, investment, or legal advice. Data is sourced from public records, industry reports, and third-party providers, and while Houzeo strives for accuracy, we make no guarantees regarding the completeness, accuracy, or timeliness of the information presented.
All estimates, projections, and historical data are based on statistical models and should not be relied upon as predictions of future market conditions. Past performance is not indicative of future results, and real estate market conditions may change due to various economic and regulatory factors. Users are responsible for conducting their own due diligence before making any real estate or financial decisions. Houzeo is not liable for any decisions or actions taken based on the information provided. Any unauthorized use, duplication, or distribution of the data may violate copyright laws and result in legal consequences. Certain information, tools and services on this page may be powered by third-party vendors. Houzeo does not control or guarantee the accuracy, reliability, or functionality of such third-party services.