| 1. |  | Sears Tower | 442,3 |
1,451 |
1974 | 3,659 | 589 |
| 2. |  | Trump Tower Chicago | 415,1 |
1,362 |
2009 | 1,091 | 216 |
| 3. |  | Aon Center | 346,3 |
1,136 |
1973 | 855 | 330 |
| 4. |  | John Hancock Center | 343,5 |
1,127 |
1969 | 1,484 | 323 |
| 5. |  | AT& T Corporate Center | 306,9 |
1,007 |
1989 | 404 | 290 |
| 6. |  | Two Prudential Plaza | 293,8 |
964 |
1990 | 810 | 150 |
| 7. |  | 311 South Wacker Drive | 292,0 |
958 |
1990 | 426 | 143 |
| 8. |  | 900 North Michigan Avenue | 265,5 |
871 |
1989 | 401 | 140 |
| 9. |  | Water Tower Place | 261,8 |
859 |
1976 | 476 | 234 |
| 10. |  | Park Tower | 260,0 |
853 |
2000 | 406 | 151 |
| 11. |  | Chase Tower | 259,1 |
850 |
1969 | 292 | 202 |
| 12. |  | Legacy at Millennium Park | 249,6 |
819 |
2010 | 123 | 32 |
| 13. |  | Aqua | 249,6 |
819 |
2009 | 874 | 109 |
| 14. |  | 300 North LaSalle | 239,3 |
785 |
2009 | 221 | 71 |
| 15. |  | Three First National Plaza | 229,5 |
753 |
1981 | 230 | 116 |
| 16. |  | Title & Trust Center | 226,0 |
741 |
1992 | 272 | 89 |
| 17. |  | One Museum Park | 223,7 |
734 |
2008 | 286 | 68 |
| 18. |  | Olympia Center | 221,0 |
725 |
1986 | 260 | 175 |
| 19. |  | 330 North Wabash | 211,8 |
695 |
1971 | 271 | 121 |
| 20. |  | UBS Tower | 210,0 |
689 |
2001 | 254 | 72 |
| 21. |  | The Elysian | 209,1 |
686 |
2009 | 157 | 46 |
| 22. |  | 111 South Wacker | 207,6 |
681 |
2005 | 322 | 83 |
| 23. |  | 181 West Madison | 207,3 |
680 |
1990 | 234 | 70 |
| 24. |  | Hyatt Center | 207,0 |
679 |
2005 | 555 | 104 |
| 25. |  | One Magnificent Mile | 205,0 |
673 |
1983 | 232 | 117 |