| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| The four stars on this Midwest city'sflagrepresent a fort, a fire & two expositions | Chicago | $1,600 | DJ | CITY FLAGS | 2019-01-03 | #7899 | |
| 2 of the 4 stars on this city's flag stand for the 1893 Columbian Exposition & the 1933 World's Fair | Chicago DD | $500 | J | FLAGS | 1991-01-31 | #1484 | |
| The 4 stars appearing on this city's flag stand for Fort Dearborn, a fire & 2 World's Fairs | Chicago | $200 | J | CITY FLAGS | 1990-03-01 | #1274 |