| Date | Grid | Clue | Author | Editor |
| Sun, Apr 14, 2024 | 68A | Home to Millennium Park | John Rippe and Jeff Chen | Fagliano |
| Tue, Dec 28, 2021 | 5D | Where Michelle Obama was born | Kathy Wienberg | Shortz |
| Sun, Sep 01, 2019 | 20A | Only musical to win Best Picture since "Oliver!" in 1968 | Finn Vigeland | Shortz |
| Thu, Feb 07, 2019 | 55D | Second-longest-running Broadway musical ever (after "The Phantom of the Opera") | Morton J. Mendelson | Shortz |
| Sat, Feb 02, 2019 | 15A | Where the term "jazz" as applied to jazz music originated | David Steinberg | Shortz |
| Tue, Dec 05, 2017 | 10D | City said to have big shoulders | Harry Smith and Zhouqin Burnikel | Shortz |
| Wed, Oct 14, 2015 | 10D | Best Picture of 2002 | Joel Fagliano | Shortz |
| Mon, Jul 01, 2013 | 10D | *The Windy City | Patrick McIntyre | Shortz |
| Sun, Jun 04, 2006 | 57A | Hit musical with the song "Razzle Dazzle" | Patrick Blindauer | Shortz |
| Sun, May 28, 1995 | 7A | "___ Poems" (Sandburg's first book) | Matt Gaffney | Shortz |
| Tue, Jul 19, 1994 | 40A | Theme of this puzzle | Christopher Hurt | Shortz |