| CHICAGO | "All That Jazz" Broadway show |
| CHICAGO | "Hard to Say I'm Sorry" rock band with a city for a name |
| CHICAGO | "If You Leave Me Now" band |
| CHICAGO | "If You Leave Me Now" rock band and recipient of the Grammy Lifetime Achievement Award in 2020 |
| CHICAGO | "_____ Poems" (Sandburg's first book) |
| CHICAGO | "the second city" |
| CHICAGO | "the windy city" |
| CHICAGO | & 12A MLB team; 2005 World Series winners |
| CHICAGO | & 1A Basketball team that won the NBA Finals three times in a row twice, from 1991-93 and 1996-98 |
| CHICAGO | 1975 Broadway musical featuring characters Velma Kelly and Roxie Hart |
| CHICAGO | 1975 Broadway musical that earned Bob Fosse three Tony nominations |
| CHICAGO | 1975 musical set in an Illinois city |
| CHICAGO | 1996 Tony-winning musical revival with the song "All That Jazz" currently playing at Broadway's Ambassador Theatre |
| CHICAGO | 2002 film starring Renee Zellweger which is named after the "Windy City" in Illinois |
| CHICAGO | 2002 musical film starring 47-Across as heiress Kitty Baxter |
| CHICAGO | America's 'Windy City' |
| CHICAGO | Band that was in the park on Fourth of July |
| CHICAGO | Band with horns |
| CHICAGO | Band with the 1984 hit "Stay the Night" |
| CHICAGO | Best Picture of 2002 |
| CHICAGO | Broadway musical with Roxie Hart and Velma Kelly |
| CHICAGO | Broadway show, movie about murderous women |
| CHICAGO | City in Illinois |
| CHICAGO | City in Illinois; Broadway musical |
| CHICAGO | City in Illinois; broadway play and movie |
| CHICAGO | City of the Bears and the Bulls |
| CHICAGO | City of the iconic red-uniformed basketball Bulls |
| CHICAGO | City said to have big shoulders |
| CHICAGO | City that is home to the Bulls and the Cubs |
| CHICAGO | City that was elegant in the past |
| CHICAGO | City whose Home Insurance Building was the first modern skyscraper |
| CHICAGO | Geographically named band with the 1984 hit "You're the Inspiration" |
| CHICAGO | Hit musical with the song "Razzle Dazzle" |
| CHICAGO | Home to Loyola and DePaul |
| CHICAGO | Home to o'hare and midway |
| CHICAGO | Illinois city known for its rap scene |
| CHICAGO | Illinois city that hosted the 39-Across in 1893 and 1933 |
| CHICAGO | Illinois city that hosts a World Marathon Majors race |
| CHICAGO | Illinois city, home to the Lincoln Park Zoo, and host of two International Conferences on Climate Change |
| CHICAGO | Largest U.S. city starting with "C" |
| CHICAGO | Largest city in the state of Illinois |
| CHICAGO | Lincoln Park Zoo city |
| CHICAGO | Loop locale |
| CHICAGO | McDonald's Thanksgiving Parade is celebrated in this city of U.S. |
| CHICAGO | Microsoft's city codename for Windows 95 |
| CHICAGO | Most populated city in the US state of Illinois |
| CHICAGO | Musical for which Catherine Zeta-Jones won an Oscar |
| CHICAGO | Musical that was elegant in the past |
| CHICAGO | Musical with a "Cell Block Tango" |
| CHICAGO | Only musical to win Best Picture since "Oliver!" in 1968 |
| CHICAGO | Oscar-winning musical starring Renée Zellweger and Richard Gere |
| CHICAGO | Port in NE Illinois, US on Lake Michigan |
| CHICAGO | Port in NE Illinois, US, on Lake Michigan |
| CHICAGO | Port in northeast Illinois, US, on Lake Michigan |
| CHICAGO | Style of thick-crust pizza |
| CHICAGO | The Windy City |
| CHICAGO | The city Kim Kardashian named her daughter after |
| CHICAGO | The ferris wheel debuted in this US city |
| CHICAGO | Theme of this puzzle |
| CHICAGO | Tina Fey, Amy Poehler did Second City improv here |
| CHICAGO | US city |
| CHICAGO | Where Bulls and Bears are cheered |
| CHICAGO | Where the term "jazz" as applied to jazz music originated |
| CHICAGO | Windy City; Broadway musical with All That Jazz |
| CHICAGO | Windy city |
| CHICAGO | Won the Academy Award for Best Movie in 2003 |
| CHICAGO | __ blues, music genre from Illinois major city |
| CHICAGO | ___ Fizz (cocktail) |
| CHICAGO | ___ Fizz, cocktail that shares part of its name with "The Windy City" |
| CHICAGO | *The Windy City |
| CHICAGO | *“Ope, we’ve got a gapers’ block” |