Most expensive homes for sale in Chicago
Written by:
November 17, 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. 457 W Deming Pl, Chicago
- Price: $4,950,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,200
- Price per square foot: $951
- Days on market: 12 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,200
- Price per square foot: $951
- Days on market: 12 days
- View listing on realtor.com
#29. 1550 N State Pkwy Unit LIB-ABC, Chicago
- Price: $4,995,000
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 8,500
- Price per square foot: $587
- Days on market: 55 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 8,500
- Price per square foot: $587
- Days on market: 55 days
- View listing on realtor.com
#28. 1407 N Hoyne Ave, Chicago
- Price: $4,995,000
- 5 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 8,250
- Price per square foot: $605
- Lot size: 0.2 acres
- Days on market: 25 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 8,250
- Price per square foot: $605
- Lot size: 0.2 acres
- Days on market: 25 days
- View listing on realtor.com
#27. 1515 N North Park Ave, Chicago
- Price: $5,200,000
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 8,400
- Price per square foot: $619
- Lot size: 0.1 acres
- Days on market: 958 days
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 8,400
- Price per square foot: $619
- Lot size: 0.1 acres
- Days on market: 958 days
- View listing on realtor.com
#26. 401 W Dickens Ave, Chicago
- Price: $5,300,000
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 7,252
- Price per square foot: $730
- Days on market: 164 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 7,252
- Price per square foot: $730
- Days on market: 164 days
- View listing on realtor.com
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#25. 452 N Morgan St, Chicago
- Price: $5,375,000
- 2 bedrooms, 2 full bathrooms, 8 half bathrooms
- Square feet: 21,170
- Price per square foot: $253
- Days on market: 59 days (-$325,000 price reduction since listing)
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 8 half bathrooms
- Square feet: 21,170
- Price per square foot: $253
- Days on market: 59 days (-$325,000 price reduction since listing)
- View listing on realtor.com
#24. 1540 N Dearborn Pkwy, Chicago
- Price: $5,495,000
- 4 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,600
- Price per square foot: $723
- Days on market: 135 days
- View listing on realtor.com
- 4 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,600
- Price per square foot: $723
- Days on market: 135 days
- View listing on realtor.com
#23. 1019 N Wolcott Ave, Chicago
- Price: $5,750,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,740
- Price per square foot: $590
- Days on market: 75 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,740
- Price per square foot: $590
- Days on market: 75 days
- View listing on realtor.com
#22. 950 N Michigan Ave Apt 4605, Chicago
- Price: $5,995,000
- 6 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 9,000
- Price per square foot: $666
- Days on market: 80 days
- View listing on realtor.com
- 6 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 9,000
- Price per square foot: $666
- Days on market: 80 days
- View listing on realtor.com
#21. 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: 747 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: 747 days
- View listing on realtor.com
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#20. 363 E Wacker Dr Unit 5806, Chicago
- Price: $6,178,474
- 4 bedrooms, 5 full bathrooms, 5 half bathrooms
- Square feet: 4,568
- Price per square foot: $1,352
- Days on market: 27 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 5 half bathrooms
- Square feet: 4,568
- Price per square foot: $1,352
- Days on market: 27 days
- View listing on realtor.com
#19. 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: 109 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: 109 days
- View listing on realtor.com
#18. 1438 N Dearborn St, Chicago
- Price: $6,500,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: not available
- Price per square foot: not available
- Days on market: 72 days (-$400,000 price reduction since listing)
- 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: 72 days (-$400,000 price reduction since listing)
- View listing on realtor.com
#17. 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: 369 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: 369 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
#16. 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: 76 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: 76 days
- View listing on realtor.com
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#15. 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: 82 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: 82 days
- View listing on realtor.com
#14. 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: 81 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: 81 days
- View listing on realtor.com
#13. 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: 34 days
- 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: 34 days
- View listing on realtor.com
#12. 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: 68 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: 68 days
- View listing on realtor.com
#11. 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: 435 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: 435 days
- View listing on realtor.com
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#10. 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: 173 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: 173 days
- View listing on realtor.com
#9. 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: 131 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: 131 days
- View listing on realtor.com
#8. 1878 N Orchard St, Chicago
- Price: $7,995,000
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 9,512
- Price per square foot: $840
- Days on market: 59 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 9,512
- Price per square foot: $840
- Days on market: 59 days
- View listing on realtor.com
#7. 14 W Superior St Unit 6900, Chicago
- Price: $7,995,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,085
- Price per square foot: $1,313
- Days on market: 300 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,085
- Price per square foot: $1,313
- Days on market: 300 days
- View listing on realtor.com
#6. 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: 115 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: 115 days
- View listing on realtor.com
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#5. 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: 684 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: 684 days (-$600,000 price reduction since listing)
- 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: 96 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: 96 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: 642 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: 642 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: 69 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: 69 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: 229 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: 229 days
- View listing on realtor.com
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