| 151. |
102,4 |
336 |
1930 |  | Century Tower |
24 | 6 |
| 152. |
101,2 |
332 |
1958 | | Inland Steel Building |
44 | 5 |
| 153. |
100,9 |
331 |
1985 | | James R. Thompson Center |
63 | 45 |
| 154. |
99,1 |
325 |
1923 | | London Guarantee Building |
45 | 7 |
| 155. |
97,8 |
321 |
2000 | | River View I |
38 | 11 |
| 156. |
92,0 |
302 |
1929 | | Riverside Plaza |
34 | 10 |
| 157. |
88,4 |
290 |
1910 | | Blackstone Hotel |
46 | 13 |
| 158. |
88,1 |
289 |
1975 | | Chicago Metropolitan Correctional Center |
47 | 22 |
| 159. |
85,3 |
280 |
2002 | | Museum Park Place |
31 | 16 |
| 160. |
83,8 |
275 |
1896 | | Fisher Building |
34 | 19 |
| 161. |
82,3 |
270 |
1951 | | Lake Shore Drive Apartments |
33 | 22 |
| 162. |
79,9 |
262 |
1931 | | Lawson YMCA |
10 | 3 |
| 163. |
76,2 |
250 |
1885 | | Dearborn Station |
44 | 10 |
| 164. |
72,5 |
238 |
1889 | | Auditorium Building |
36 | 9 |
| 165. |
64,6 |
212 |
1894 | | Old Colony Building |
35 | 17 |
| 166. |
63,4 |
208 |
1927 | | 10 West Elm |
38 | 12 |
| 167. |
63,1 |
207 |
1904 | | Carson Pirie Scott Company Department Store |
48 | 13 |
| 168. |
61,0 |
200 |
1895 | | Reliance Building |
39 | 12 |
| 169. |
55,0 |
180 |
1885 | | Home Insurance Building |
0 | 0 |
| 170. |
46,9 |
154 |
1869 | | Chicago Water Tower |
137 | 22 |
| 171. |
|
|
1992 | | Sheraton Chicago Hotel & Towers |
29 | 15 |
| 172. |
|
|
1991 | | Harold Washington Library Center |
42 | 18 |
| 173. |
|
|
1986 | | 225 West Washington Street |
32 | 9 |
| 174. |
|
|
1977 | | Apparel Center |
14 | 11 |
| 175. |
|
|
1925 | | Union Station |
62 | 15 |
| 176. |
|
|
1921 | | Chicago Theater |
74 | 14 |
| 177. |
|
|
1914 | | Central Office Building |
36 | 14 |
| 178. |
|
|
1912 | | Franklin Building |
6 | 2 |
| 179. |
|
|
1904 | | Santa Fe Building |
28 | 14 |
| 180. |
|
|
1888 | | Rookery Building |
51 | 25 |
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