| # | 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 | Tribune East | 1,422 ft | 113 | skyscraper | 2024 | ||
| 5 | Waldorf=Astoria | 3 | 1,265 ft | 107 | skyscraper | 2010 | |
| 6 | 400 Lake Shore Drive - South Tower | 1,100 ft | 76 | skyscraper | 2023 | ||
| 7 | 400 Lake Shore Drive - North Tower | 850 ft | 65 | skyscraper | 2023 | ||
| 8 | One Bennett Park | 4 | 837 ft | 67 | skyscraper | 2019 | |
| 9 | Cityfront Center Plaza | 704 ft | 62 | skyscraper | - | ||
| 10 | Lake Point Tower | 93 | 645 ft | 70 | skyscraper | 1968 | |
| 11 | River East Center | 32 | 644 ft | 58 | skyscraper | 2001 | |
| 12 | River East Center II | 644 ft | 58 | skyscraper | - | ||
| 13 | NBC Tower | 29 | 627 ft | 37 | skyscraper | 1989 | |
| 14 | Optima Signature | 5 | 588 ft | 54 | skyscraper | 2017 | |
| 15 | 150 East Ontario | 2 | 588 ft | 51 | skyscraper | - | |
| 16 | 474 North Lake Shore Drive | 11 | 581 ft | 61 | skyscraper | 1990 | |
| 17 | Axis | 8 | 570 ft | 58 | skyscraper | 1986 | |
| 18 | Loews Hotel/North Water Apartments | 7 | 569 ft | 50 | skyscraper | 2015 | |
| 19 | Atwater Apartments | 163 | 554 ft | 55 | skyscraper | 2009 | |
| 20 | 600 North Lake Shore Drive | 1 | 544 ft | 49 | skyscraper | 1999 |