| # | Building | City | Floors | Height | Year | |
|---|---|---|---|---|---|---|
| 1 | Willis Tower | Chicago | 108 | 1,451 ft | 1974 | |
| 2 | Trump International Hotel & Tower | Chicago | 98 | 1,388 ft | 2009 | |
| 3 | St. Regis Chicago | Chicago | 95 | 1,191 ft | 2021 | |
| 4 | Aon Center | Chicago | 83 | 1,136 ft | 1973 | |
| 5 | 875 North Michigan Avenue | Chicago | 100 | 1,128 ft | 1969 | |
| 6 | Franklin Center North Tower | Chicago | 60 | 1,007 ft | 1989 | |
| 7 | Two Prudential Plaza | Chicago | 64 | 995 ft | 1990 | |
| 8 | 311 South Wacker | Chicago | 65 | 961 ft | 1990 | |
| 9 | NEMA Chicago | Chicago | 76 | 896 ft | 2019 | |
| 10 | 900 North Michigan | Chicago | 66 | 871 ft | 1989 | |
| 11 | Water Tower Place | Chicago | 74 | 859 ft | 1976 | |
| 12 | Aqua | Chicago | 86 | 859 ft | 2009 | |
| 13 | Chase Tower | Chicago | 60 | 850 ft | 1969 | |
| 14 | Park Tower | Chicago | 67 | 844 ft | 2000 | |
| 15 | One Bennett Park | Chicago | 67 | 837 ft | 2019 | |
| 16 | The Legacy at Millennium Park | Chicago | 73 | 819 ft | 2010 | |
| 17 | 110 North Wacker Drive | Chicago | 55 | 815 ft | 2020 | |
| 18 | 300 North LaSalle | Chicago | 60 | 785 ft | 2009 | |
| 19 | 70 West Madison | Chicago | 57 | 767 ft | 1981 | |
| 20 | Grant Thornton Tower | Chicago | 50 | 756 ft | 1992 | |