Most expensive homes for sale in Chicago
Written by:
September 22, 2025
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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.
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#30. 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
- Days on market: 180 days
- View listing on realtor.com
- 3 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $922
- Days on market: 180 days
- View listing on realtor.com
#29. 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: 291 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: 291 days
- View listing on realtor.com
#28. 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: 684 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: 684 days
- View listing on realtor.com
#27. 451 W Superior St, Chicago
- Price: $6,250,000
- 5 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,179
- Price per square foot: $614
- Days on market: 66 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,179
- Price per square foot: $614
- Days on market: 66 days
- View listing on realtor.com
#26. 363 E Wacker Dr Unit 6106, Chicago
- Price: $6,450,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,708
- Price per square foot: $1,370
- Days on market: 46 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,708
- Price per square foot: $1,370
- Days on market: 46 days
- View listing on realtor.com
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#25. 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: 306 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: 306 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
#24. 1964 N Burling St, Chicago
- Price: $6,500,000
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,800
- Price per square foot: $955
- Days on market: 13 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,800
- Price per square foot: $955
- Days on market: 13 days
- View listing on realtor.com
#23. 159 E Walton Pl Apt 31A, Chicago
- Price: $6,750,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,500
- Price per square foot: $1,227
- Days on market: 19 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 5,500
- Price per square foot: $1,227
- Days on market: 19 days
- View listing on realtor.com
#22. 1438 N Dearborn St, Chicago
- Price: $6,900,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: not available
- Price per square foot: not available
- Days on market: 9 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: not available
- Price per square foot: not available
- Days on market: 9 days
- View listing on realtor.com
#21. 451 E Grand Ave Apt 6111, Chicago
- Price: $6,900,000
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,798
- Price per square foot: $1,438
- Days on market: 18 days
- View listing on realtor.com
- 3 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,798
- Price per square foot: $1,438
- Days on market: 18 days
- View listing on realtor.com
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#20. 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: 179 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: 179 days
- View listing on realtor.com
#19. 800 N Michigan Ave Unit 63PH, Chicago
- Price: $6,950,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 8,400
- Price per square foot: $827
- Days on market: 90 days (-$750,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 8,400
- Price per square foot: $827
- Days on market: 90 days (-$750,000 price reduction since listing)
- View listing on realtor.com
#18. 1865 N Burling St, Chicago
- Price: $6,950,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,000
- Price per square foot: $1,158
- Days on market: 17 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,000
- Price per square foot: $1,158
- Days on market: 17 days
- View listing on realtor.com
#17. 363 E Wacker Dr Unit 7501, Chicago
- Price: $6,950,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,212
- Days on market: 62 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,212
- Days on market: 62 days
- View listing on realtor.com
#16. 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: 372 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: 372 days
- View listing on realtor.com
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#15. 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: 110 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: 110 days
- View listing on realtor.com
#14. 189 E Lake Shore Dr Ste 18, Chicago
- Price: $7,250,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 7,462
- Price per square foot: $971
- Days on market: 68 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 7,462
- Price per square foot: $971
- Days on market: 68 days
- View listing on realtor.com
#13. 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: 108 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: 108 days
- View listing on realtor.com
#12. 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: 90 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: 90 days
- View listing on realtor.com
#11. 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
- Days on market: 164 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 4 half bathrooms
- Square feet: 7,523
- Price per square foot: $1,050
- Days on market: 164 days
- View listing on realtor.com
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#10. 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: 237 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: 237 days
- View listing on realtor.com
#9. 363 E Wacker Dr Unit 9101, Chicago
- Price: $7,999,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,395
- Days on market: 52 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,395
- Days on market: 52 days
- View listing on realtor.com
#8. 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
- Days on market: 222 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,500
- Price per square foot: $1,066
- Days on market: 222 days
- View listing on realtor.com
#7. 1878 N Orchard St, Chicago
- Price: $8,790,000
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 9,512
- Price per square foot: $924
- Days on market: 61 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 9,512
- Price per square foot: $924
- Days on market: 61 days
- View listing on realtor.com
#6. 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: 621 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: 621 days (-$600,000 price reduction since listing)
- View listing on realtor.com
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#5. 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
- Days on market: 121 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 8,300
- Price per square foot: $1,078
- Days on market: 121 days
- View listing on realtor.com
#4. 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
- Days on market: 33 days
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 8,691
- Price per square foot: $1,087
- Days on market: 33 days
- View listing on realtor.com
#3. 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: 579 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: 579 days
- View listing on realtor.com
#2. 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: 6 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: 6 days
- View listing on realtor.com
#1. 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
- Days on market: 166 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 13,400
- Price per square foot: $1,380
- Days on market: 166 days
- View listing on realtor.com
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