Most expensive homes for sale in Chicago
Written by:
March 25, 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. 1845 N Orchard St, Chicago
- Price: $5,495,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,380
- Price per square foot: $655
- Lot size: 0.1 acres
- Days on market: 24 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,380
- Price per square foot: $655
- Lot size: 0.1 acres
- Days on market: 24 days
- View listing on realtor.com
#29. 1841 N Orchard St, Chicago
- Price: $5,850,000
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,380
- Price per square foot: $698
- Lot size: 0.0 acres
- Days on market: 97 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,380
- Price per square foot: $698
- Lot size: 0.0 acres
- Days on market: 97 days
- View listing on realtor.com
#28. 1540 N Dearborn Pkwy, Chicago
- Price: $5,950,000
- 4 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,600
- Price per square foot: $782
- Lot size: 0.1 acres
- Days on market: 272 days
- View listing on realtor.com
- 4 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,600
- Price per square foot: $782
- Lot size: 0.1 acres
- Days on market: 272 days
- View listing on realtor.com
#27. 2217 N Fremont St, Chicago
- Price: $5,950,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,081
- Lot size: 0.1 acres
- Days on market: 409 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,081
- Lot size: 0.1 acres
- Days on market: 409 days
- View listing on realtor.com
#26. 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: 242 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: 242 days
- View listing on realtor.com
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#25. 401 W Dickens Ave, Chicago
- Price: $5,995,000
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 7,252
- Price per square foot: $826
- Lot size: 0.2 acres
- Days on market: 19 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 7,252
- Price per square foot: $826
- Lot size: 0.2 acres
- Days on market: 19 days
- View listing on realtor.com
#24. 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: 109 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: 109 days
- View listing on realtor.com
#23. 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: 502 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: 502 days
- View listing on realtor.com
#22. 1524 N Astor St, Chicago
- Price: $6,395,000
- 3 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $983
- Lot size: 0.1 acres
- Days on market: 250 days
- View listing on realtor.com
- 3 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $983
- Lot size: 0.1 acres
- Days on market: 250 days
- View listing on realtor.com
#21. 1515 N State Pkwy, Chicago
- Price: $6,995,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,680
- Price per square foot: $722
- Lot size: 0.1 acres
- Days on market: 109 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,680
- Price per square foot: $722
- Lot size: 0.1 acres
- Days on market: 109 days
- View listing on realtor.com
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#20. 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: 17 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: 17 days
- View listing on realtor.com
#19. 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: 190 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: 190 days
- View listing on realtor.com
#18. 11 E Walton St Ph 58, Chicago
- Price: $6,995,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,600
- Price per square foot: $1,249
- Days on market: 157 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,600
- Price per square foot: $1,249
- Days on market: 157 days
- View listing on realtor.com
#17. 2210 N Orchard St, Chicago
- Price: $7,450,000
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,975
- Price per square foot: $934
- Lot size: 0.2 acres
- Days on market: 150 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,975
- Price per square foot: $934
- Lot size: 0.2 acres
- Days on market: 150 days
- View listing on realtor.com
#16. 445 W Superior St, Chicago
- Price: $7,500,000
- 6 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 10,800
- Price per square foot: $694
- Lot size: 0.1 acres
- Days on market: 39 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 10,800
- Price per square foot: $694
- Lot size: 0.1 acres
- Days on market: 39 days
- View listing on realtor.com
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#15. 460 W Huron St, Chicago
- Price: $7,500,000
- 7 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 10,360
- Price per square foot: $723
- Lot size: 0.2 acres
- Days on market: 124 days
- View listing on realtor.com
- 7 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 10,360
- Price per square foot: $723
- Lot size: 0.2 acres
- Days on market: 124 days
- View listing on realtor.com
#14. 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: 61 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: 61 days
- View listing on realtor.com
#13. 2334 N Cleveland St, Chicago
- Price: $7,750,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,409
- Days on market: 59 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,500
- Price per square foot: $1,409
- Days on market: 59 days
- View listing on realtor.com
#12. 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: 55 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: 55 days
- View listing on realtor.com
#11. 363 E Wacker Dr Unit 7501, Chicago
- Price: $7,995,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,394
- Days on market: 167 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,734
- Price per square foot: $1,394
- Days on market: 167 days
- View listing on realtor.com
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#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: 40 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: 40 days
- View listing on realtor.com
#9. 209 E Lake Shore Dr Unit 14, Chicago
- Price: $8,450,000
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 12,250
- Price per square foot: $689
- Days on market: 6 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 12,250
- Price per square foot: $689
- Days on market: 6 days
- View listing on realtor.com
#8. 9 W Walton St Apt 3600, Chicago
- Price: $8,500,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,500
- Price per square foot: $1,133
- Days on market: 55 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,500
- Price per square foot: $1,133
- Days on market: 55 days
- View listing on realtor.com
#7. 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: 439 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: 439 days (-$600,000 price reduction since listing)
- 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: 397 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: 397 days
- View listing on realtor.com
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#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: 646 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: 646 days
- View listing on realtor.com
#4. 363 E Wacker Dr Unit 8801, Chicago
- Price: $11,519,240
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,156
- Price per square foot: $1,871
- Days on market: 829 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 6,156
- Price per square foot: $1,871
- Days on market: 829 days
- View listing on realtor.com
#3. 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: 249 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: 249 days
- View listing on realtor.com
#2. 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: 244 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: 244 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: 143 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: 143 days
- View listing on realtor.com
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