| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| Chicago's street addresses emanate from Point Zero, the intersection of Madison Avenue & this street | State Street | $600 | J | HIGHWAYS & BYWAYS | 2006-11-24 | #5110 | |
| In song, it's Chicago's "Great Street" where "they do things they don't do on Broadway" | State Street | $200 | DJ | HIGHWAYS & BYWAYS | 1988-04-13 | #843 | |
| In song about "that toddling town", it's Chicago's "great street" | State Street | $400 | DJ | HIGHWAY & BYWAYS | 1987-05-19 | #637 |