| # | Building | Images | Height | Floors | Building type | Year | Status |
|---|---|---|---|---|---|---|---|
| 1 | Chicago Spire | 493 | 2,000 ft | 150 | skyscraper | - | |
| 2 | Chicago Tower | 2,000 ft | - | telecommunications tower | 2011 | ||
| 3 | Old Post Office Tower I | 2,000 ft | 170 | skyscraper | 2022 | ||
| 4 | Gateway Tower | 2,000 ft | - | skyscraper | - | ||
| 5 | Beitler Tower | 2,000 ft | - | telecommunications tower | - | ||
| 6 | Miglin-Beitler Skyneedle | 1 | 2,000 ft | 125 | skyscraper | 1988 | |
| 7 | Project 2000 | 1,969 ft | 120 | skyscraper | - | ||
| 8 | Wolf Point | 1,745 ft | 142 | skyscraper | - | ||
| 9 | Thompson Center Redevelopment | 1,700 ft | 115 | skyscraper | - | ||
| 10 | 7 South Dearborn | 4 | 1,567 ft | 112 | skyscraper | 2004 | |
| 11 | Willis Tower | 95 | 1,451 ft | 108 | skyscraper | 1974 | |
| 12 | Tribune East | 1,422 ft | 102 | skyscraper | 2025 | ||
| 13 | Trump International Hotel & Tower | 2520 | 1,388 ft | 98 | skyscraper | 2009 | |
| 14 | One North Wacker | 1,275 ft | 83 | skyscraper | - | ||
| 15 | Waldorf-Astoria Chicago | 3 | 1,265 ft | 107 | skyscraper | 2010 | |
| 16 | Madison Canal Office Tower 1 | 1,215 ft | 90 | skyscraper | 1969 | ||
| 17 | St. Regis Chicago | 31 | 1,191 ft | 95 | skyscraper | 2021 | |
| 18 | Aon Center | 65 | 1,136 ft | 83 | skyscraper | 1973 | |
| 19 | Dearborn Center | 1,135 ft | 85 | skyscraper | - | ||
| 20 | 875 North Michigan Avenue | 104 | 1,128 ft | 100 | skyscraper | 1969 |