| 100% | AON | 3 | ___ Center (Chicago skyscraper) |
| 100% | AON | 3 | __ Center: Chicago skyscraper |
| 91% | AON | 3 | Chicago's __ Center skyscraper |
| 73% | AON | 3 | ___ Center (Chicago skyscraper named for an insurance broker) |
| 64% | AON | 3 | Chicago's ___ Center |
| 64% | AON | 3 | Chicago's __ Center |
| 63% | WILLIS | 6 | __ Tower, Chicago skyscraper, aka Sears Tower |
| 63% | SEARS | 5 | Former name on a Chicago skyscraper |
| 62% | DALEY | 5 | Chicago's Richard ___ Center |
| 61% | AON | 3 | __ Center: L.A. skyscraper |
| 59% | ARENA | 5 | Chicago's United Center, for one |
| 58% | ARTHOUSE | 8 | Chicago's Siskel Film Center, for instance |
| 58% | AON | 3 | ___ Center, second-tallest building in Chicago |
| 57% | AQUA | 4 | 859 ft high Chicago skyscraper with a unique undulating appearance |
| 56% | LOOP | 4 | Historical center of Chicago, with The |
| 55% | AON | 3 | Chicago's ___ Center, formerly known as the Amoco Building |
| 54% | BULL | 4 | Hoops player at Chicago's United Center |
| 54% | DOME | 4 | Rounded feature of the Chicago Cultural Center |
| 53% | STAINED | 7 | Like the domes in the Chicago Cultural Center |
| 49% | UNITED | 6 | ___ Center, indoor arena home to the Chicago Blackhawks and the Chicago Bulls |
| 48% | OBAMA | 5 | His presidential center is being built on Chicago's South Side |
| 48% | PCA | 3 | 2025 NL All-Star center fielder for the Chicago Cubs, informally |
| 48% | AON | 3 | London-based insurance giant with eponymous Chicago and L.A. skyscrapers |
| 47% | AON | 3 | ___ Center (Chicago's second-tallest building) |
| 46% | OBAMA | 5 | His presidential center will be built on the south side of Chicago |
| 43% | BULL | 4 | NBA player from Chicago who would play a home game at the United Center |
| 39% | TALL | 4 | Like a skyscraper |
| 39% | TENSTORY | 8 | Like a skyscraper |
| 39% | ERECTS | 6 | Builds a skyscraper |
| 39% | LOFTY | 5 | Like a skyscraper |