| # | Building | Images | Height | Floors | Building type | Year | Status |
|---|---|---|---|---|---|---|---|
| 1 | Chicago Spire | 493 | 2,000 ft | 150 | skyscraper | - | |
| 2 | Gateway Tower | 2,000 ft | - | skyscraper | - | ||
| 3 | Beitler Tower | 2,000 ft | - | telecommunications tower | - | ||
| 4 | Project 2000 | 1,969 ft | 120 | skyscraper | - | ||
| 5 | Wolf Point | 1,745 ft | 142 | skyscraper | - | ||
| 6 | Tribune East | 1,422 ft | 102 | skyscraper | 2025 | ||
| 7 | Trump International Hotel & Tower | 2520 | 1,388 ft | 98 | skyscraper | 2009 | |
| 8 | Waldorf-Astoria Chicago | 3 | 1,265 ft | 107 | skyscraper | 2010 | |
| 9 | 875 North Michigan Avenue | 104 | 1,128 ft | 100 | skyscraper | 1969 | |
| 10 | 400 Lake Shore Drive - South Tower | 1,100 ft | 76 | skyscraper | 2023 | ||
| 11 | One Chicago Tower A | 2 | 971 ft | 76 | skyscraper | 2021 | |
| 12 | 900 North Michigan | 39 | 871 ft | 66 | skyscraper | 1989 | |
| 13 | Water Tower Place | 30 | 859 ft | 74 | skyscraper | 1976 | |
| 14 | InterContinental Chicago Hotel North | 850 ft | 71 | skyscraper | - | ||
| 15 | 400 Lake Shore Drive - North Tower | 850 ft | 65 | skyscraper | 2023 | ||
| 16 | Park Tower | 38 | 844 ft | 67 | skyscraper | 2000 | |
| 17 | One Bennett Park | 10 | 837 ft | 67 | skyscraper | 2019 | |
| 18 | Salesforce Tower | 1 | 813 ft | 58 | skyscraper | 2023 | |
| 19 | 300 North LaSalle | 441 | 785 ft | 60 | skyscraper | 2009 | |
| 20 | Wolf Point Apartments | 782 ft | 80 | skyscraper | 1963 |