| Clue | Answer |
| Chicago's Tallest building (Current Name) | |
| Chicago's Second Tallest | |
| Street that seperates east/west Chicago | |
| Street that seperates north/south | |
| There is a Chicago street named after each of the 5 great lakes, Name the one that has a different directional orientation than the rest. | |
| Cubs biggest rival | |
| Bears biggest rival | |
| Blackhawks biggest rival | |
| Team White Sox beat in 2005 world series. | |
| | Clue | Answer |
| Besides Pippen and Jordan, Name a player that started for the 1996 72-10 Chicago Bulls. | |
| What is the only train you can ride from Wrigley Field to US Cellular? | |
| Highway Named after 34th president | |
| Highway named after runner up of same presidential election | |
| College nicknamed 'Flames' | |
| Event that occured in October 1871 | |
| Biggest tourist destination in Illinois | |
| 'Big East' School | |
| Only Residential Building east of Lakeshore Drive | |
|