Apartment Price Drops This Week in South Side - Chicago, IL
Biggest Rent Drops in South Side, Chicago
Data updated: September 24, 2025 at 04:25 PM PDT
Looking for an apartment deal in South Side? We’ve surfaced the biggest rent drops and current trends in this part of Chicago.
Which listings in South Side have had the biggest price drops in the past week?
Unit 02 at 5508 S. Cornell Avenue features 4 bedrooms and 3 bathrooms and recently had its price reduced by $300, bringing it down to $2999. Meanwhile, Unit 5700-1 at 5700 S. Blackstone Avenue offers 4 bedrooms and 2 bathrooms, with a recent price drop of $211, now listed at $3999. These deals represent significant savings on spacious properties, making them worth exploring for anyone in the market for a new home.
| Property Name | Unit Description | New Price (Drop) | Drop Date |
|---|---|---|---|
| 5508 S. Cornell Avenue | 4 beds, 3 baths | $2999 (-$300) | 9/18 |
| 5700 S. Blackstone Avenue | 4 beds, 2 baths | $3999 (-$211) | 9/22 |
| Del Prado | 2 beds, 1 bath | $2185 (-$185) | 9/23 |
| Windermere House | 1 bed, 2 baths | $2285 (-$170) | 9/23 |
| Prairie Shores | 1 bed, 1 bath | $1360 (-$149) | 9/22 |
| Lake Meadows | 2 beds, 1 bath | $1395 (-$140) | 9/19 |
| 5457-5459 S. Blackstone Avenue | 1 bed, 1 bath | $1490 (-$135) | 9/22 |
| 5252 | 2 beds, 2 baths | $3995 (-$125) | 9/22 |
| Regents Park | 2 beds, 2 baths | $2375 (-$120) | 9/18 |
| 5335-5337 S. Woodlawn Avenue | 5 beds, 2 baths | $4095 (-$104) | 9/22 |
What’s the rent trend in South Side?
Rent trend data is not available for this neighborhood at the moment.
Top 5 Price Drops This Week
5508 S. Cornell Avenue – 02
4 beds, 3 baths, 1920 sq ft
Was: $3299 → Now: $2999
Price Drop: $300
Price Changed on: 9/18
5700 S. Blackstone Avenue – 5700-1
4 beds, 2 baths, 2265 sq ft
Was: $4210 → Now: $3999
Price Drop: $211
Price Changed on: 9/22
Del Prado – 403
2 beds, 1 bath, 823 sq ft
Was: $2370 → Now: $2185
Price Drop: $185
Price Changed on: 9/23
Windermere House – 1006
1 bed, 2 baths, 1032 sq ft
Was: $2455 → Now: $2285
Price Drop: $170
Price Changed on: 9/23
Prairie Shores – 1-1308
1 bed, 1 bath, 620 sq ft
Was: $1509 → Now: $1360
Price Drop: $149
Price Changed on: 9/22
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Note: Pricing, availability, and specials are subject to change. Please check the individual listings for the most up-to-date information.
