Chi Town Lady is one of three winners out of Toni's Hollyday (Harlan's Holiday), a stakes-placed triple winner, and is the first black-type performer among her four runners.

Second dam May Day Vow (Broken Vow) won two Listed races and has seven winners from eight other runners.

Third dam May Day Bluff (Pine Bluff) never raced and produced five other winners, among them May Day Rose (Rockport Harbor), a dual Grade 3 winner placed at Grade 2 level. Her daughter Roman Bluff (Roman Ruler) is the dam of Flying Frank, a Listed-placed winner of 17 races, and of the dual Listed-placed winner Easy Money.

Her two-year-old son Quincy Cafe (Mendelssohn) has since got off the mark, and she also has a yearling colt by Liam's Map and a filly foal by Game Winner. She was then covered by Not This Time.