Most expensive homes for sale in Chicago
Written by:
July 7, 2025
scarp577 // Shutterstock
Most expensive homes for sale in Chicago
Stacker compiled a list of the most expensive homes in Chicago listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
You may also like:
Highest-rated restaurants in Chicago by diners
#30. 1407 N Hoyne Ave, Chicago
- Price: $5,995,000
- 5 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 10,250
- Price per square foot: $584
- Lot size: 0.2 acres
- Days on market: 347 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 10,250
- Price per square foot: $584
- Lot size: 0.2 acres
- Days on market: 347 days
- View listing on realtor.com
#29. 1019 N Wolcott Ave, Chicago
- Price: $5,995,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,740
- Price per square foot: $615
- Lot size: 0.2 acres
- Days on market: 16 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,740
- Price per square foot: $615
- Lot size: 0.2 acres
- Days on market: 16 days
- View listing on realtor.com
#28. 1524 N Astor St, Chicago
- Price: $5,995,000
- 3 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $922
- Lot size: 0.1 acres
- Days on market: 103 days
- View listing on realtor.com
- 3 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $922
- Lot size: 0.1 acres
- Days on market: 103 days
- View listing on realtor.com
#27. 21 N May St Apt 1502, Chicago
- Price: $5,995,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,187
- Price per square foot: $1,155
- Days on market: 214 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,187
- Price per square foot: $1,155
- Days on market: 214 days
- View listing on realtor.com
#26. 401 N Wabash Ave Unit 86A, Chicago
- Price: $6,000,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,029
- Price per square foot: $1,489
- Days on market: 607 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,029
- Price per square foot: $1,489
- Days on market: 607 days
- View listing on realtor.com
You may also like:
Chicago 7-day weather forecast
#25. 2123 N Bissell St, Chicago
- Price: $6,250,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,700
- Price per square foot: $718
- Lot size: 0.1 acres
- Days on market: 26 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,700
- Price per square foot: $718
- Lot size: 0.1 acres
- Days on market: 26 days
- View listing on realtor.com
#24. 460 W Huron St, Chicago
- Price: $6,500,000
- 7 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 10,360
- Price per square foot: $627
- Lot size: 0.2 acres
- Days on market: 229 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 10,360
- Price per square foot: $627
- Lot size: 0.2 acres
- Days on market: 229 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
#23. 363 E Wacker Dr Unit 6106, Chicago
- Price: $6,750,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,708
- Price per square foot: $1,433
- Days on market: 33 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,708
- Price per square foot: $1,433
- Days on market: 33 days
- View listing on realtor.com
#22. 9 W Walton St Apt 2802, Chicago
- Price: $6,900,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $1,533
- Days on market: 102 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,500
- Price per square foot: $1,533
- Days on market: 102 days
- View listing on realtor.com
#21. 1970 N Burling St, Chicago
- Price: $6,995,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 7,800
- Price per square foot: $896
- Lot size: 0.1 acres
- Days on market: 122 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 7,800
- Price per square foot: $896
- Lot size: 0.1 acres
- Days on market: 122 days
- View listing on realtor.com
You may also like:
Highest-rated Italian restaurants in Chicago by diners
#20. 451 E Grand Ave Apt Ph 66, Chicago
- Price: $6,995,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,147
- Price per square foot: $978
- Days on market: 295 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,147
- Price per square foot: $978
- Days on market: 295 days
- View listing on realtor.com
#19. 363 E Wacker Dr Unit 6306, Chicago
- Price: $6,995,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,850
- Price per square foot: $1,442
- Days on market: 33 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,850
- Price per square foot: $1,442
- Days on market: 33 days
- View listing on realtor.com
#18. 2043 N Clifton Ave, Chicago
- Price: $7,150,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,790
- Price per square foot: $917
- Lot size: 0.2 acres
- Days on market: 30 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,790
- Price per square foot: $917
- Lot size: 0.2 acres
- Days on market: 30 days
- View listing on realtor.com
#17. 363 E Wacker Dr Unit 7501, Chicago
- Price: $7,495,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,307
- Days on market: 37 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,307
- Days on market: 37 days
- View listing on realtor.com
#16. 2334 N Cleveland St, Chicago
- Price: $7,500,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,363
- Days on market: 31 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,363
- Days on market: 31 days
- View listing on realtor.com
You may also like:
Highest-paying management jobs for people in Chicago
#15. 800 N Michigan Ave Unit 63PH, Chicago
- Price: $7,700,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 8,400
- Price per square foot: $916
- Days on market: 13 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 8,400
- Price per square foot: $916
- Days on market: 13 days
- View listing on realtor.com
#14. 800 N Michigan Ave Unit 60PHN, Chicago
- Price: $7,700,000
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,000
- Price per square foot: $1,925
- Days on market: 90 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 4,000
- Price per square foot: $1,925
- Days on market: 90 days
- View listing on realtor.com
#13. 209 E Lake Shore Dr Unit 14, Chicago
- Price: $7,900,000
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 12,250
- Price per square foot: $644
- Days on market: 13 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 12,250
- Price per square foot: $644
- Days on market: 13 days
- View listing on realtor.com
#12. 79 E Cedar St, Chicago
- Price: $7,900,000
- 4 bedrooms, 5 full bathrooms, 4 half bathrooms
- Square feet: 7,523
- Price per square foot: $1,050
- Lot size: 0.0 acres
- Days on market: 87 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 4 half bathrooms
- Square feet: 7,523
- Price per square foot: $1,050
- Lot size: 0.0 acres
- Days on market: 87 days
- View listing on realtor.com
#11. 14 W Superior St Unit 6900, Chicago
- Price: $7,995,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 6,085
- Price per square foot: $1,313
- Days on market: 160 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 6,085
- Price per square foot: $1,313
- Days on market: 160 days
- View listing on realtor.com
You may also like:
Highest-rated steak restaurants in the Chicago area by diners
#10. 1865 N Fremont St, Chicago
- Price: $8,000,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,500
- Price per square foot: $1,066
- Lot size: 0.1 acres
- Days on market: 145 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,500
- Price per square foot: $1,066
- Lot size: 0.1 acres
- Days on market: 145 days
- View listing on realtor.com
#9. 159 E Walton Pl Unit Ph, Chicago
- Price: $8,900,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 7,880
- Price per square foot: $1,129
- Days on market: 544 days (-$600,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 7,880
- Price per square foot: $1,129
- Days on market: 544 days (-$600,000 price reduction since listing)
- View listing on realtor.com
#8. 1534 N Dearborn Pkwy, Chicago
- Price: $8,950,000
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 8,300
- Price per square foot: $1,078
- Lot size: 0.1 acres
- Days on market: 44 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 8,300
- Price per square foot: $1,078
- Lot size: 0.1 acres
- Days on market: 44 days
- View listing on realtor.com
#7. 1853 N Burling St, Chicago
- Price: $9,450,000
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 8,691
- Price per square foot: $1,087
- Lot size: 0.1 acres
- Days on market: 75 days
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 8,691
- Price per square foot: $1,087
- Lot size: 0.1 acres
- Days on market: 75 days
- View listing on realtor.com
#6. 2026 N Kenmore Ave, Chicago
- Price: $9,995,000
- 10 bedrooms, 8 full bathrooms, 2 half bathrooms
- Square feet: 13,400
- Price per square foot: $745
- Lot size: 0.2 acres
- Days on market: 502 days
- View listing on realtor.com
- 10 bedrooms, 8 full bathrooms, 2 half bathrooms
- Square feet: 13,400
- Price per square foot: $745
- Lot size: 0.2 acres
- Days on market: 502 days
- View listing on realtor.com
You may also like:
Highest-paying computer and engineering jobs in Chicago
#5. 1867 N Burling St, Chicago
- Price: $10,000,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,000
- Price per square foot: $1,111
- Lot size: 0.1 acres
- Days on market: 751 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,000
- Price per square foot: $1,111
- Lot size: 0.1 acres
- Days on market: 751 days
- View listing on realtor.com
#4. 800 N Michigan Ave Ph 64, Chicago
- Price: $11,700,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,500
- Price per square foot: $1,376
- Days on market: 354 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,500
- Price per square foot: $1,376
- Days on market: 354 days
- View listing on realtor.com
#3. 800 N Michigan Ave Ph 67, Chicago
- Price: $15,750,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,250
- Price per square foot: $1,702
- Days on market: 349 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,250
- Price per square foot: $1,702
- Days on market: 349 days
- View listing on realtor.com
#2. 915 N Dearborn St, Chicago
- Price: $18,500,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 13,400
- Price per square foot: $1,380
- Lot size: 0.1 acres
- Days on market: 89 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 13,400
- Price per square foot: $1,380
- Lot size: 0.1 acres
- Days on market: 89 days
- View listing on realtor.com
#1. 1355 N Astor St, Chicago
- Price: $21,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 25,000
- Price per square foot: $840
- Lot size: 0.3 acres
- Days on market: 248 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 25,000
- Price per square foot: $840
- Lot size: 0.3 acres
- Days on market: 248 days
- View listing on realtor.com
You may also like:
Highest-rated delis in Chicago by diners
