| Question | Answer |
| Lake _________ | |
| River that runs through Downtown | |
| County in which Chicago lies | |
| State in which Chicago lies | |
| Country in which Chicago lies | |
| Chicago's First Permanent Resident | |
| Former Fort in Chicago | |
| Incorporation Year | |
| Year Union Stockyards Opened | |
| Year of Chicago Fire | |
| Name of the 1893 World's Fair | |
| Name of the 1933 World's Fair | |
| Northside Baseball Team | |
| Southside Baseball Team | |
| Football Team | |
| Hockey Team | |
| Basketball Team | |
| Soccer Team | |
| | Question | Answer |
| Famous Department Store | |
| Airport | |
| Airport | |
| Former Airport | |
| Former Tallest Building in the World | |
| Tower that Survived Chicago Fire | |
| 22nd Street | |
| Crawford Ave. | |
| 12th Street | |
| 39th Street | |
| Magnificent Mile | |
| First Mayor of Chicago | |
| Famous Chicago Gangster | |
| Railroad Baron | |
| Mayor from 1955-1976 | |
| President Whose Home is in Chicago | |
| Founder of Hull-House | |
|