| 101. |
146,0 |
479 |
1929 | | 33 North LaSalle |
4 | 2 |
| 102. |
145,1 |
476 |
1927 | | Bankers Building |
42 | 12 |
| 103. |
144,8 |
475 |
1965 | | Cook County Administration Building |
12 | 19 |
| 104. |
144,8 |
475 |
1924 | | Metropolitan Tower |
51 | 14 |
| 105. |
144,5 |
474 |
1924 | | Lake Shore Place |
44 | 14 |
| 106. |
143,6 |
471 |
1929 | | Hotel Inter-Continental |
48 | 10 |
| 107. |
143,3 |
470 |
1990 | | City Place |
59 | 13 |
| 108. |
142,0 |
466 |
2006 | | The Regatta |
43 | 18 |
| 109. |
142,0 |
466 |
2001 | | The Sterling |
45 | 13 |
| 110. |
142,0 |
466 |
1997 | | Blue Cross-Blue Shield Building |
45 | 14 |
| 111. |
141,7 |
465 |
1929 | | Randolph Tower |
46 | 14 |
| 112. |
141,0 |
463 |
1925 | | Tribune tower |
268 | 72 |
| 113. |
140,5 |
461 |
1986 | | Presidential towers |
87 | 18 |
| 114. |
139,6 |
458 |
2008 | | 600 North Fairbanks |
14 | 3 |
| 115. |
139,3 |
457 |
1989 | | Swissotel Chicago |
35 | 14 |
| 116. |
139,3 |
457 |
1965 | | 401 North Michigan Avenue |
13 | 7 |
| 117. |
139,0 |
456 |
2007 | | Kingsbury Plaza |
11 | 2 |
| 118. |
138,4 |
454 |
2003 | | 400 North LaSalle |
38 | 17 |
| 119. |
138,1 |
453 |
2003 | | ABN AMRO Plaza |
22 | 5 |
| 120. |
137,8 |
452 |
1925 | | Roanoke Building |
15 | 9 |
| 121. |
137,5 |
451 |
2002 | | Riverbend |
41 | 8 |
| 122. |
137,2 |
450 |
2005 | | The Shoreham |
32 | 15 |
| 123. |
137,2 |
450 |
1987 | | Eugenie Terrace on the Park |
39 | 6 |
| 124. |
135,6 |
445 |
1971 | | 300 South Wacker |
38 | 7 |
| 125. |
133,5 |
438 |
1929 | | Willoughby Tower |
43 | 11 |
| 126. |
132,6 |
435 |
1988 | | 123 N. Wacker Drive |
38 | 8 |
| 127. |
132,0 |
433 |
1989 | | 225 West Wacker Drive |
33 | 6 |
| 128. |
130,1 |
427 |
1990 | | American Medical Association Headquarters |
54 | 8 |
| 129. |
129,5 |
425 |
2006 | | Sky55 |
61 | 15 |
| 130. |
128,3 |
421 |
2003 | | Skybridge |
49 | 12 |
| 131. |
126,5 |
415 |
2002 | | 2 East Erie |
5 | 2 |
| 132. |
124,7 |
409 |
2006 | | Museum Tower |
49 | 8 |
| 133. |
123,1 |
404 |
1968 | | Time-Life Building |
7 | 4 |
| 134. |
121,3 |
398 |
1924 | | Wrigley Building |
193 | 57 |
| 135. |
120,7 |
396 |
1928 | | 333 North Michigan Avenue |
39 | 8 |
| 136. |
120,4 |
395 |
2003 | | The Pearson |
7 | 1 |
| 137. |
119,8 |
393 |
1970 | | 150 North Wacker |
29 | 15 |
| 138. |
118,3 |
388 |
2002 | | Wells Street Tower |
30 | 15 |
| 139. |
118,0 |
387 |
2003 | | Forty-One East Eighth |
32 | 11 |
| 140. |
117,3 |
385 |
1960 | | Executive Plaza |
24 | 11 |
| 141. |
116,4 |
382 |
1992 | | Cityfront Place |
26 | 11 |
| 142. |
115,2 |
378 |
2003 | | The Residences at Grand Plaza |
35 | 6 |
| 143. |
111,9 |
367 |
2004 | | 1111 South Wabash |
2 | 1 |
| 144. |
111,6 |
366 |
2004 | | Left Bank at K Station |
17 | 10 |
| 145. |
111,3 |
365 |
2001 | | Kinzie Park Tower |
16 | 13 |
| 146. |
109,7 |
360 |
2000 | | Chestnut Tower |
6 | 4 |
| 147. |
109,7 |
360 |
1924 | | Allerton Hotel |
38 | 11 |
| 148. |
105,8 |
347 |
2002 | | Sofitel Chicago Water Tower |
47 | 6 |
| 149. |
103,6 |
340 |
1931 | | Merchandise Mart |
74 | 12 |
| 150. |
103,6 |
340 |
1927 | | Chicago Hilton and Towers |
42 | 20 |