Rosie is a freckled, red-haired thirteen-year-old girl with a spunky personality. She narrates the family's journey to Chicago. While confident on her home turf, the overwhelming environment of the big city and the fair makes her timid. She is observant and eager to learn, though her lack of worldly experience occasionally leads to awkward social situations.

At seventeen, Lottie is a pretty and strong-minded girl who proves highly capable at managing domestic duties. She is older and more sophisticated than her siblings, demonstrating a keen instinct for reading social situations. She uses her confidence and astuteness to guide her aunt through difficult moments in the city.

Silas Fuller is an elderly, mischievous man with a fondness for country sayings and a rebellious streak. He frequently disrupts the overly refined atmosphere of his daughter's Chicago home with his loud behavior and plainspoken manners. He brings his dog Tip everywhere and uses his age to excuse his refusal to conform to strict social expectations.

Euterpe is a wealthy, forty-four-year-old widow living in a grand Chicago house. A former secretary who married her employer, she is ostracized by high society and hides her intense loneliness behind heavy mourning veils. She is deeply intimidated by her own household staff and desperately longs for social acceptance.

LeRoy "Buster" Beckett is an energetic seven-year-old boy who idolizes his grandfather. He is elusive and quick, often disappearing from his family to explore his own interests at the fair. He hates dressing up for the city and strongly prefers the freedom of rural life.

Adelaide is a thirty-eight-year-old farm mother with a practical mindset and a strict hand in running her household. She is intimidated by the prospect of visiting the big city, choosing instead to remain behind in Illinois. She harbors strong suspicions about the hired men who court her eldest daughter.

Gideon is a hardworking, forty-year-old farmer who runs the Beckett family homestead. He possesses a dry sense of humor and maintains a deep respect for his wife's practical decisions.

Everett is a hired hand working in rural Christian County for the summer. He is pale and relatively unknown to the local community, which makes Lottie's mother highly suspicious of his background and intentions.

Mrs. O'Shay is Aunt Euterpe's rude and lazy cook. Hired by the late Mr. Fleischacker, she openly disrespects her current employer and serves poor-quality food, taking advantage of Euterpe's timid nature.

Flanagan is the carriage driver for the Fleischacker household. He guides the carriage through the bustling, paved streets of Chicago but is poorly managed by his timid employer.

Tip is Granddad Fuller's loyal and energetic dog. He constantly accompanies his owner, despises being left behind, and frequently causes chaotic disruptions during public events.

Bertha Palmer is the wealthy and influential President of the Board of Lady Managers for the fair. She acts as the unofficial hostess and ultimate gatekeeper of Chicago's high society, deciding who is accepted into elite circles.

Colonel Cody is a celebrated showman who stages spectacular arena performances featuring cowboys, Indigenous Americans, wild ponies, and sharpshooters. He is charismatic and commands immense respect from the massive fair crowds.

Lillian Russell is a famous, highly glamorous singer and actress. Despite her immense public popularity, she faces harsh judgment and exclusion from Chicago's strict upper-class matrons due to her divorces and theatrical profession.

Mrs. Evans is the elegant wife of a dean at the University of Chicago. She acts as a respected member of the city's upper class, hosting musical evenings and formal social gatherings.