| Hint | Answer | % Correct |
|---|---|---|
| Lake on which Chicago lies | Lake Michigan | 95%
|
| Chicago's most famous nickname | The {Windy} City | 91%
|
| What you must never put on a Chicago-style hotdog | Ketchup | 87%
|
| Largest airport | O'Hare | 87%
|
| Tallest building | Willis Tower | 86%
|
| U.S. President who lived in Chicago | Barack Obama | 82%
|
| Movie character who skipped school to experience Chicago | Ferris Bueller | 73%
|
| Key feature of Chicago-style pizza | Deep-dish | 68%
|
| Highest circulation newspaper | Chicago Tribune | 58%
|
| University located in Evanston | Northwestern | 57%
|
| Most famous TV host | Oprah Winfrey | 54%
|
| Chicago's trains are known as "The El". What is "El" short for? | Elevated | 52%
|
| Singer who said Chicago is his kind of town | Frank Sinatra | 52%
|
| Most famous rapper | Kanye West | 51%
|
| The baddest part of town, according to Jim Croce | The South Side | 47%
|
| Chicago's central business district | The {Loop} | 46%
|
| Park where the Bean is located | Millennium Park | 39%
|
| Chicago's aquarium, once the largest in the world | Shedd Aquarium | 35%
|
| Woman whose cow supposedly started the Chicago fire | Mrs. O'Leary | 34%
|
| Chicago's most famous shopping district | {Magnificent} Mile | 33%
|
| Father / son mayors who led Chicago from 1955–1976 and 1989–2001 | Richard J. Daley / Richard M. Daley | 31%
|
| Most famous comedy club | Second City | 29%
|
| Park where Buckingham Fountain is located | Grant Park | 24%
|