The most expensive neighborhoods in Chicago
Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Chicago metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. Downtown Hinsdale (Hinsdale, IL)
Median sale price: $2,225,000 | Median days on market: 108 days13 S Elm St, Hinsdale, IL 60521
- List price: $3,995,000
- Beds: 5 | Baths: 4.5 | Square feet: 6,074
- See 13 S Elm St, Hinsdale, IL 60521 on Redfin.com
28 S Clay St, Hinsdale, IL 60521
- List price: $1,100,000
- Beds: 3 | Baths: 3.5 | Square feet: 2,701
- See 28 S Clay St, Hinsdale, IL 60521 on Redfin.com
6 S Elm St, Hinsdale, IL 60521
- List price: $2,995,000
- Beds: 5 | Baths: 5.5 | Square feet: 4,340
- See 6 S Elm St, Hinsdale, IL 60521 on Redfin.com
#2. Timber Trails (Western Springs, IL)
Median sale price: $1,600,000 | Median days on market: 43 days5903 Timber Trails Blvd, Western Springs, IL 60558
- List price: $1,698,420
- Beds: 5 | Baths: 4.5 | Square feet: 5,000
- See 5903 Timber Trails Blvd, Western Springs, IL 60558 on Redfin.com
5912 Cottonwood Ct, Western Springs, IL 60558
- List price: $1,599,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,850
- See 5912 Cottonwood Ct, Western Springs, IL 60558 on Redfin.com
6008 Burr Oak Dr, Western Springs, IL 60558
- List price: $1,599,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,850
- See 6008 Burr Oak Dr, Western Springs, IL 60558 on Redfin.com
#3. Lakeshore (Evanston, IL)
Median sale price: $1,417,500 | Median days on market: 46 days1120 Forest Ave, Evanston, IL 60202
- List price: $2,699,000
- Beds: 7 | Baths: 6 | Square feet: 8,360
- See 1120 Forest Ave, Evanston, IL 60202 on Redfin.com
1319 Forest Ave, Evanston, IL 60201
- List price: $3,995,000
- Beds: 5 | Baths: 6 | Square feet: 5,418
- See 1319 Forest Ave, Evanston, IL 60201 on Redfin.com
202 Greenwood St, Evanston, IL 60201
- List price: $2,995,000
- Beds: 7 | Baths: 6.5 | Square feet: 7,500
- See 202 Greenwood St, Evanston, IL 60201 on Redfin.com
225 Hamilton St, Evanston, IL 60202
- List price: $2,095,000
- Beds: 6 | Baths: 5 | Square feet: 5,416
- See 225 Hamilton St, Evanston, IL 60202 on Redfin.com
#4. Horner Park (Chicago, IL)
Median sale price: $1,362,500 | Median days on market: 34 days2415 W Belle Plaine Ave, Chicago, IL 60618
- List price: $1,325,000
- Beds: 5 | Baths: 4.5 | Square feet: 3,900
- See 2415 W Belle Plaine Ave, Chicago, IL 60618 on Redfin.com
#5. Ashwood Park (Naperville, IL)
Median sale price: $1,187,500 | Median days on market: 71 days4052 Teak Cir, Naperville, IL 60564
- List price: $1,249,900
- Beds: 5 | Baths: 5 | Square feet: 6,094
- See 4052 Teak Cir, Naperville, IL 60564 on Redfin.com
4215 Chinaberry Ln, Naperville, IL 60564
- List price: $1,000,100
- Beds: 4 | Baths: 3 | Square feet: 3,500
- See 4215 Chinaberry Ln, Naperville, IL 60564 on Redfin.com
4240 Chinaberry Ln, Naperville, IL 60564
- List price: $1,300,000
- Beds: 5 | Baths: 5 | Square feet: 3,338
- See 4240 Chinaberry Ln, Naperville, IL 60564 on Redfin.com
4447 Sassafras Ln, Naperville, IL 60564
- List price: $1,349,900
- Beds: 5 | Baths: 4.5 | Square feet: 4,883
- See 4447 Sassafras Ln, Naperville, IL 60564 on Redfin.com
