| 1. |
442,3 |
1,451 |
1974 | | Sears Tower |
1,503 | 322 |
| 2. |
415,1 |
1,362 |
2009 | | Trump Tower Chicago |
113 | 21 |
| 3. |
346,3 |
1,136 |
1973 | | Aon Center |
392 | 149 |
| 4. |
343,5 |
1,127 |
1969 | | John Hancock Center |
613 | 162 |
| 5. |
306,9 |
1,007 |
1989 | | AT& T Corporate Center |
171 | 114 |
| 6. |
293,8 |
964 |
1990 | | Two Prudential Plaza |
373 | 76 |
| 7. |
292,0 |
958 |
1990 | | 311 South Wacker Drive |
172 | 67 |
| 8. |
265,5 |
871 |
1989 | | 900 North Michigan Avenue |
178 | 52 |
| 9. |
261,8 |
859 |
1976 | | Water Tower Place |
184 | 85 |
| 10. |
260,0 |
853 |
2000 | | Park Tower |
173 | 64 |
| 11. |
259,1 |
850 |
1969 | | Chase Tower |
114 | 87 |
| 12. |
249,6 |
819 |
2010 | | Aqua |
101 | 12 |
| 13. |
239,3 |
785 |
2009 | | 300 North LaSalle |
29 | 7 |
| 14. |
229,5 |
753 |
1981 | | Three First National Plaza |
113 | 57 |
| 15. |
226,0 |
741 |
1992 | | Title & Trust Center |
134 | 46 |
| 16. |
223,7 |
734 |
2008 | | One Museum Park |
36 | 4 |
| 17. |
221,0 |
725 |
1986 | | Olympia Center |
112 | 74 |
| 18. |
211,8 |
695 |
1971 | | 330 North Wabash |
121 | 50 |
| 19. |
210,0 |
689 |
2001 | | UBS Tower |
108 | 29 |
| 20. |
209,1 |
686 |
2009 | | The Elysian |
11 | 4 |
| 21. |
207,6 |
681 |
2005 | | 111 South Wacker |
179 | 37 |
| 22. |
207,3 |
680 |
1990 | | 181 West Madison |
129 | 29 |
| 23. |
207,0 |
679 |
2005 | | Hyatt Center |
315 | 50 |
| 24. |
205,0 |
673 |
1983 | | One Magnificent Mile |
124 | 47 |
| 25. |
204,8 |
672 |
2007 | | 340 on the Park |
93 | 57 |
| 26. |
203,6 |
668 |
1992 | | United Building |
149 | 34 |
| 27. |
197,5 |
648 |
1965 | | Daley Center |
83 | 54 |
| 28. |
197,2 |
647 |
2004 | | 55 East Erie |
96 | 34 |
| 29. |
196,6 |
645 |
1968 | | Lake Point Tower |
400 | 73 |
| 30. |
196,3 |
644 |
2001 | | River East Center I |
103 | 24 |
| 31. |
195,4 |
641 |
2003 | | Grand Plaza Apartments |
69 | 31 |
| 32. |
194,5 |
638 |
2009 | | 155 North Wacker |
24 | 5 |
| 33. |
193,5 |
635 |
1989 | | Leo Burnett Company HQ |
71 | 33 |
| 34. |
192,3 |
631 |
2005 | | Heritage at Millennium Park |
87 | 29 |
| 35. |
190,2 |
624 |
2009 | | 353 North Clark |
7 | 1 |
| 36. |
185,0 |
607 |
1990 | | Chicago Place |
72 | 22 |
| 37. |
184,4 |
605 |
1930 | | Chicago Board of Trade Building |
118 | 28 |
| 38. |
183,5 |
602 |
1989 | | NBC Tower |
109 | 30 |
| 39. |
183,2 |
601 |
1972 | | CNA Plaza |
112 | 48 |
| 40. |
183,2 |
601 |
1955 | | Prudential Building |
108 | 46 |
| 41. |
183,0 |
600 |
1992 | | Heller International Tower |
65 | 24 |
| 42. |
182,6 |
599 |
1982 | | Madison Plaza |
36 | 15 |
| 43. |
181,4 |
595 |
2003 | | Millennium Centre |
57 | 42 |
| 44. |
179,8 |
590 |
1964 | | 1000 Lake Shore Plaza |
30 | 22 |
| 45. |
179,5 |
589 |
2008 | | The Clare at Water Tower |
4 | 3 |
| 46. |
179,2 |
588 |
1964 | | Marina City |
409 | 83 |
| 47. |
178,6 |
586 |
1987 | | Citigroup Center |
108 | 19 |
| 48. |
177,4 |
582 |
1984 | | Smurfit-Stone Building |
437 | 67 |
| 49. |
177,0 |
581 |
1991 | | North Pier Apartment Tower |
55 | 52 |
| 50. |
177,0 |
581 |
1972 | | Mid Continental Plaza |
67 | 29 |