| # | Building | Images | Height | Floors | Building type | Year | Status |
|---|---|---|---|---|---|---|---|
| 1 | Columbian Exposition Administration Building | 278 ft | - | monumental hall | 1893 | ||
| 2 | Manufactures Building | 237 ft | - | hall | 1893 | ||
| 3 | Obama Presidential Center | 235 ft | 8 | high-rise building | 2021 | ||
| 4 | Logan Center for Creative & Performing Arts | 170 ft | 11 | high-rise building | 2012 | ||
| 5 | David M. Rubenstein Forum | 165 ft | 10 | high-rise building | 2020 | ||
| 6 | Midway Gardens Apartments | 4 | 162 ft | 17 | high-rise building | 1953 | |
| 7 | The Study at the University of Chicago | 155 ft | 13 | high-rise building | 2021 | ||
| 8 | 6400 South Stony Island | ≈396 ft | 34 | high-rise building | - | ||
| 9 | Island Terrace Apartments | 1 | ≈245 ft | 21 | high-rise building | 1969 | |
| 10 | Smith-Blair House | 1 | ≈210 ft | 18 | high-rise building | 1980 | |
| 11 | Woodlawn Residential Commons | ≈186 ft | 16 | high-rise building | 2020 | ||
| 12 | Jackson Park Terrace | 10 | ≈175 ft | 15 | high-rise building | 1974 | |
| 13 | Stonehenge Apartment Hotel | ≈140 ft | 12 | high-rise building | 1929 | ||
| 14 | Wedgewood Hotel | ≈140 ft | 12 | high-rise building | - | ||
| 15 | Washington Scene | ≈116 ft | 10 | low-rise building | - | ||
| 16 | Park Station Lofts | ≈116 ft | 10 | low-rise building | - | ||
| 17 | 6054 South Drexel Avenue | ≈116 ft | 10 | low-rise building | 2008 | ||
| 18 | University of Chicago Faculty Apartments | 1 | ≈116 ft | 10 | low-rise building | 1949 | |
| 19 | Ada S. McKinley Apartments | ≈105 ft | 9 | low-rise building | - | ||
| 20 | University House | ≈105 ft | 9 | low-rise building | - |