The highest-value homes in Chicago

Every city has its showpiece homes — the ones that define luxury living. And as prices continue to rise across the U.S., the most valuable properties showcase just how high local markets can go. The high-end housing market in particular has reached new heights in 2025, with the typical luxury home selling for a record $1.35 million in March. The million-dollar price tag no longer even qualifies as "luxury" in most places.

So, what do Chicago's most glamorous homes look like? To find out, Redfin Real Estate found the city's highest-value homes based on their Redfin Estimate.

#1. 1932 N Burling St, Chicago, IL 60614
- Approximate home value: $20,051,352
- Beds: not available
- Baths: not available
- Square feet: not available
- See 1932 N Burling St, Chicago, IL 60614 on Redfin.com

#2. 915 N Dearborn St, Chicago, IL 60610
- Approximate home value: $16,908,770
- Beds: 6
- Baths: 6
- Square feet: 13,400
- See 915 N Dearborn St, Chicago, IL 60610 on Redfin.com

#3. 65 E Goethe St, Chicago, IL 60610
- Approximate home value: $15,517,195
- Beds: 6
- Baths: 8.5
- Square feet: not available
- See 65 E Goethe St, Chicago, IL 60610 on Redfin.com

#4. 363 E Wacker Dr, Chicago, IL 60601
- Approximate home value: $15,054,980
- Beds: not available
- Baths: not available
- Square feet: not available
- See 363 E Wacker Dr, Chicago, IL 60601 on Redfin.com

#5. 1955 N Burling St, Chicago, IL 60614
- Approximate home value: $14,305,509
- Beds: 9
- Baths: 7
- Square feet: 8,758
- See 1955 N Burling St, Chicago, IL 60614 on Redfin.com

#6. 400 W Dickens Ave, Chicago, IL 60614
- Approximate home value: $13,200,042
- Beds: 6
- Baths: 6.5
- Square feet: 9,937
- See 400 W Dickens Ave, Chicago, IL 60614 on Redfin.com

#7. 1950 N Burling St, Chicago, IL 60614
- Approximate home value: $12,199,532
- Beds: 4
- Baths: 4.5
- Square feet: 4,942
- See 1950 N Burling St, Chicago, IL 60614 on Redfin.com

#8. 9 W Walton St, Chicago, IL 60610
- Approximate home value: $12,121,335
- Beds: not available
- Baths: not available
- Square feet: not available
- See 9 W Walton St, Chicago, IL 60610 on Redfin.com

#9. 1919 N Howe St, Chicago, IL 60614
- Approximate home value: $11,994,789
- Beds: 7
- Baths: 8.5
- Square feet: 9,928
- See 1919 N Howe St, Chicago, IL 60614 on Redfin.com

#10. 1909 N Orchard St, Chicago, IL 60614
- Approximate home value: $11,714,888
- Beds: not available
- Baths: not available
- Square feet: not available
- See 1909 N Orchard St, Chicago, IL 60614 on Redfin.com

#11. 1955 N Orchard St, Chicago, IL 60614
- Approximate home value: $11,445,414
- Beds: 10
- Baths: 9
- Square feet: 19,716
- See 1955 N Orchard St, Chicago, IL 60614 on Redfin.com

#12. 800 N Michigan Ave, Chicago, IL 60611
- Approximate home value: $11,394,972
- Beds: 5
- Baths: 6
- Square feet: 8,500
- See 800 N Michigan Ave, Chicago, IL 60611 on Redfin.com

#13. 1926 N Burling St, Chicago, IL 60614
- Approximate home value: $11,381,181
- Beds: 6
- Baths: 9
- Square feet: 15,533
- See 1926 N Burling St, Chicago, IL 60614 on Redfin.com

#14. 1905 N Orchard St, Chicago, IL 60614
- Approximate home value: $11,211,487
- Beds: not available
- Baths: not available
- Square feet: not available
- See 1905 N Orchard St, Chicago, IL 60614 on Redfin.com

#15. 401 N Wabash Ave, Chicago, IL 60611
- Approximate home value: $11,021,029
- Beds: not available
- Baths: not available
- Square feet: not available
- See 401 N Wabash Ave, Chicago, IL 60611 on Redfin.com

Methodology

Redfin Estimate data as of September 11, 2025. Bedroom, bathroom, and square footage data may not be available or accurate. Secondary addresses may not be included. Value estimates may not reflect what the house could actually sell for.