| Five-time Kentucky Derby winner |
| Five-time world champion figure skater Carol |
| Peter ___ (Chicago singer and bassist) |
| Chicago university |
| Chicago's Little Village, e.g. |
| Chicago N.F.L. team |
| Adele won five of them in February |
| Five-time teammate of Bryant, Duncan, and Nowitzki at the NBA All-Star Game |
| Chicago's locale |
| Attend a party uninvited ... and a literal hint to five sets of circled letters |
| Chicago ballplayer |
| Chicago's United Center e.g. |
| Film title character who likes to high-five |
| Two of five expanses |
| Actor Richard of "Unfaithful" and "Chicago |
| Setting for Chicago's Summerfest: Abbr. |
| Chicago's ___ Center |
| My father had a small estate in Nottinghamshire; I was the third of five sons |
| Part of five Declaration of Independence signatures |
| Against (which appears amidst the five long Across answers) |
| Chicago P.D." detective Lindsay |
| Famed Chicago hotel |
| And you even managed to do 24 ___ in the strip mall parking lot, when the sign clearly said Five Guys Burgers and Fries... |
| Anagrammy-winning song about Chicago's favorite outdoor sport? |
| Chicago's Peter |
| 1983 song with the lyric "Let's leave Chicago to the Eskimos |
| Five-time MLB All-Star Cooper |
| '60s sitcom setup, part 3: Then the five passengers and two crewmen became ___ |
| Actor on "Homicide: Life on the Street" and "Chicago P.D. |
| Chicago-area institution home to the world's most powerful particle accelerator |