Most expensive homes for sale in Chicago

Written by:
February 18, 2025
Konstantin L // 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.

#30. 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: 74 days
- View listing on realtor.com

#29. 1211 S Prairie Ave Apt 5400, Chicago

- Price: $5,999,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 10,000
- Price per square foot: $599
- Days on market: 60 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: 467 days
- View listing on realtor.com

#27. 401 W Dickens Ave, Chicago

- Price: $6,250,000
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 7,252
- Price per square foot: $861
- Lot size: 0.2 acres
- Days on market: 96 days
- View listing on realtor.com

#26. 1856 N Mohawk St, Chicago

- Price: $6,390,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 8,700
- Price per square foot: $734
- Lot size: 0.1 acres
- Days on market: 171 days
- View listing on realtor.com

#25. 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: 215 days
- View listing on realtor.com

#24. 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: 74 days
- View listing on realtor.com

#23. 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: 151 days
- View listing on realtor.com

#22. 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: 155 days
- View listing on realtor.com

#21. 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: 122 days
- View listing on realtor.com

#20. 1521 N State Pkwy, Chicago

- Price: $7,290,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,700
- Price per square foot: $751
- Lot size: 0.1 acres
- Days on market: 213 days
- View listing on realtor.com

#19. 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: 115 days
- View listing on realtor.com

#18. 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: 4 days
- View listing on realtor.com

#17. 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: 89 days
- View listing on realtor.com

#16. 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: 26 days
- View listing on realtor.com

#15. 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: 24 days
- View listing on realtor.com

#14. 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: 20 days
- View listing on realtor.com

#13. 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: 132 days
- View listing on realtor.com

#12. 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: 5 days
- View listing on realtor.com

#11. 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: 20 days
- View listing on realtor.com

#10. 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: 404 days (-$600,000 price reduction since listing)
- View listing on realtor.com

#9. 209 E Lake Shore Dr Unit 14, Chicago

- Price: $9,500,000
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 12,250
- Price per square foot: $775
- Days on market: 166 days (-$400,000 price reduction since listing)
- View listing on realtor.com

#8. 14 W Superior St Unit 7200, Chicago

- Price: $9,500,000
- 3 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 6,085
- Price per square foot: $1,561
- Days on market: 564 days
- View listing on realtor.com

#7. 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: 362 days
- View listing on realtor.com

#6. 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: 611 days
- View listing on realtor.com

#5. 4 E Elm St Ph 23, Chicago

- Price: $10,800,000
- 4 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 5,400
- Price per square foot: $2,000
- Days on market: 194 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: 794 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: 214 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: 209 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: 108 days
- View listing on realtor.com

Trending Now