Based on the popular American Girl franchise, the game puts the player in control of Kit Kittredge, a clever and resourceful girl growing up in the 1930s. As the Great Depression went into full swing, things became hard for the Kittredge family, forcing Kit's dad to close down their car dealership business and go to Chicago to seek work, with the rest of the family doing a number of odd jobs, such as taking in boarders and selling eggs, in order to survive.
Like in the Nancy Drew series of games, the game revolves around roaming the neighbourhood, interrogating people, and gathering clues as well as information. The game is presented in an open third-person perspective, which, unlike in most mystery adventure games, allows players to roam around in full 3D instead of just clicking on various objects in order to progress through the game.