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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 in 2025, with the typical luxury home selling for a record $1.35 million in March. The million-dollar price tag even qualifies as "luxury" in most places.

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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

#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

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.