1. Six North Michigan Avenue (The Tower Building; Montgomery Ward & Company Building – The Loop) – 282′; tallest building in Chicago: 1899-1922
2. The Wrigley Building (Streeterville) – 425′; tallest building in Chicago: 1922-1924
3. Chicago Temple Building (The Loop) – 568′; tallest building in Chicago: 1924-1930
4. Chicago Board of Trade Building (The Loop) – 605′; tallest building in Chicago: 1930-1965
5. Richard J. Daley Center (The Loop) – 648′; tallest building in Chicago: 1965-1969
6. John Hancock Center (875 North Michigan Avenue – Streeterville) – 1,127′; tallest building in Chicago: 1969-1973
7. Aon Center (The Loop) – 1,136′; formerly known as the Standard Oil Building; tallest building in Chicago: 1973-1974
8. Sears Tower (Willis Tower – The Loop)- 1,451′; 3rd-tallest building in the United States; 26th-tallest building in the world; tallest building in the world: 1974-1998)