| # | Gebäude | Bilder | Höhe | Etagen | Gebäudetyp | Jahr | Status |
|---|---|---|---|---|---|---|---|
| 1 | Chicago Spire | 493 | 2.000 ft | 150 | Wolkenkratzer | - | |
| 2 | Chicago Tower | 2.000 ft | - | Fernsehturm | 2011 | ||
| 3 | Old Post Office Tower I | 2.000 ft | 170 | Wolkenkratzer | 2022 | ||
| 4 | Gateway Tower | 2.000 ft | - | Wolkenkratzer | - | ||
| 5 | Beitler Tower | 2.000 ft | - | Fernsehturm | - | ||
| 6 | Miglin-Beitler Skyneedle | 1 | 2.000 ft | 125 | Wolkenkratzer | 1988 | |
| 7 | Project 2000 | 1.969 ft | 120 | Wolkenkratzer | - | ||
| 8 | Wolf Point | 1.745 ft | 142 | Wolkenkratzer | - | ||
| 9 | 7 South Dearborn | 4 | 1.567 ft | 112 | Wolkenkratzer | 2004 | |
| 10 | Willis Tower | 93 | 1.451 ft | 108 | Wolkenkratzer | 1974 | |
| 11 | Tribune East | 1.422 ft | 102 | Wolkenkratzer | 2025 | ||
| 12 | Trump International Hotel & Tower | 2514 | 1.388 ft | 98 | Wolkenkratzer | 2009 | |
| 13 | One North Wacker | 1.275 ft | 83 | Wolkenkratzer | - | ||
| 14 | Waldorf-Astoria Chicago | 3 | 1.265 ft | 107 | Wolkenkratzer | 2010 | |
| 15 | Madison Canal Office Tower 1 | 1.215 ft | 90 | Wolkenkratzer | 1969 | ||
| 16 | St. Regis Chicago | 31 | 1.191 ft | 95 | Wolkenkratzer | 2021 | |
| 17 | Aon Center | 65 | 1.136 ft | 83 | Wolkenkratzer | 1973 | |
| 18 | Dearborn Center | 1.135 ft | 85 | Wolkenkratzer | - | ||
| 19 | 875 North Michigan Avenue | 103 | 1.128 ft | 100 | Wolkenkratzer | 1969 | |
| 20 | 400 Lake Shore Drive - South Tower | 1.100 ft | 76 | Wolkenkratzer | 2023 |