| 1. |
442,3 |
1,451 |
1974 | | Sears Tower |
1,824 | 377 |
| 2. |
415,1 |
1,362 |
2009 | | Trump Tower Chicago |
230 | 68 |
| 3. |
346,3 |
1,136 |
1973 | | Aon Center |
450 | 170 |
| 4. |
343,5 |
1,127 |
1969 | | John Hancock Center |
721 | 184 |
| 5. |
306,9 |
1,007 |
1989 | | AT& T Corporate Center |
196 | 132 |
| 6. |
293,8 |
964 |
1990 | | Two Prudential Plaza |
444 | 92 |
| 7. |
292,0 |
958 |
1990 | | 311 South Wacker Drive |
200 | 79 |
| 8. |
265,5 |
871 |
1989 | | 900 North Michigan Avenue |
211 | 62 |
| 9. |
261,8 |
859 |
1976 | | Water Tower Place |
209 | 102 |
| 10. |
260,0 |
853 |
2000 | | Park Tower |
201 | 74 |
| 11. |
259,1 |
850 |
1969 | | Chase Tower |
134 | 96 |
| 12. |
249,6 |
819 |
2010 | | Aqua |
183 | 42 |
| 13. |
239,3 |
785 |
2009 | | 300 North LaSalle |
55 | 22 |
| 14. |
229,5 |
753 |
1981 | | Three First National Plaza |
127 | 65 |
| 15. |
226,0 |
741 |
1992 | | Title & Trust Center |
150 | 50 |
| 16. |
223,7 |
734 |
2008 | | One Museum Park |
82 | 38 |
| 17. |
221,0 |
725 |
1986 | | Olympia Center |
129 | 87 |
| 18. |
211,8 |
695 |
1971 | | 330 North Wabash |
137 | 58 |
| 19. |
210,0 |
689 |
2001 | | UBS Tower |
126 | 39 |
| 20. |
209,1 |
686 |
2009 | | The Elysian |
32 | 10 |
| 21. |
207,6 |
681 |
2005 | | 111 South Wacker |
203 | 55 |
| 22. |
207,3 |
680 |
1990 | | 181 West Madison |
146 | 40 |
| 23. |
207,0 |
679 |
2005 | | Hyatt Center |
355 | 72 |
| 24. |
205,0 |
673 |
1983 | | One Magnificent Mile |
140 | 56 |
| 25. |
204,8 |
672 |
2007 | | 340 on the Park |
110 | 67 |
| 26. |
203,6 |
668 |
1992 | | United Building |
166 | 50 |
| 27. |
197,5 |
648 |
1965 | | Daley Center |
96 | 62 |
| 28. |
197,2 |
647 |
2004 | | 55 East Erie |
104 | 44 |
| 29. |
196,6 |
645 |
1968 | | Lake Point Tower |
465 | 86 |
| 30. |
196,3 |
644 |
2001 | | River East Center I |
113 | 34 |
| 31. |
195,4 |
641 |
2003 | | Grand Plaza Apartments |
77 | 39 |
| 32. |
194,5 |
638 |
2009 | | 155 North Wacker |
37 | 12 |
| 33. |
193,5 |
635 |
1989 | | Leo Burnett Company HQ |
80 | 39 |
| 34. |
192,3 |
631 |
2005 | | Heritage at Millennium Park |
100 | 49 |
| 35. |
190,2 |
624 |
2009 | | 353 North Clark |
18 | 12 |
| 36. |
185,0 |
607 |
1990 | | Chicago Place |
85 | 28 |
| 37. |
184,4 |
605 |
1930 | | Chicago Board of Trade Building |
147 | 34 |
| 38. |
183,5 |
602 |
1989 | | NBC Tower |
131 | 37 |
| 39. |
183,2 |
601 |
1972 | | CNA Plaza |
132 | 61 |
| 40. |
183,2 |
601 |
1955 | | Prudential Building |
121 | 60 |
| 41. |
183,0 |
600 |
1992 | | Heller International Tower |
74 | 29 |
| 42. |
182,6 |
599 |
1982 | | Madison Plaza |
47 | 19 |
| 43. |
181,4 |
595 |
2003 | | Millennium Centre |
63 | 47 |
| 44. |
179,8 |
590 |
1964 | | 1000 Lake Shore Plaza |
37 | 33 |
| 45. |
179,5 |
589 |
2008 | | The Clare at Water Tower |
20 | 11 |
| 46. |
179,2 |
588 |
1964 | | Marina City |
457 | 96 |
| 47. |
178,6 |
586 |
1987 | | Citigroup Center |
128 | 23 |
| 48. |
177,4 |
582 |
1984 | | Smurfit-Stone Building |
521 | 90 |
| 49. |
177,0 |
581 |
1991 | | North Pier Apartment Tower |
63 | 62 |
| 50. |
177,0 |
581 |
1972 | | Mid Continental Plaza |
73 | 43 |