Miles is a sixteen-year-old boy who moves from Florida to a boarding school in Alabama called Culver Creek. He has a fascination with reading biographies and memorizing the famous last words of historical figures. Unpopular in his hometown, he embraces his new environment and quickly integrates into a circle of intelligent, rebellious friends.

Chip, universally known as the Colonel, is Miles's confident and proactive roommate. Admitted to the school on a scholarship, he possesses a sharp intellect and a talent for memorizing the names of countries and capital cities. He acts as the strategic mastermind behind the group's pranks and holds a deep-seated grudge against the wealthy students who go home on weekends, known as the Weekday Warriors.

Alaska is a beautiful and highly unpredictable student at Culver Creek. She reads voraciously and maintains an expansive personal library in her dorm room, prioritizing experiencing life over finishing her books immediately. Despite her lively exterior and propensity for planning creative mischief, she exhibits sudden mood swings that puzzle her peers.

Takumi is a talkative and energetic member of Chip and Alaska's friend group. He possesses a talent for freestyle rapping and often provides comic relief, though he also displays a strong investigative streak. He is determined to discover who reported Alaska's former roommate to the administration.

Lara is a Romanian immigrant student at Culver Creek who becomes part of Alaska's extended social circle. She is sweet-natured but sometimes struggles with verbal communication, having spent much of her early life in America translating and handling adult responsibilities for her parents.

Mr. Starnes is the strict dean of students at Culver Creek, universally referred to by the students as the Eagle. He lives in the dorm circle and possesses an uncanny ability to catch students breaking the rules. He presides over the student jury system and acts as the final judge on disciplinary matters.

Dr. Hyde is an elderly, strict World Religions teacher at Culver Creek. He suffers from ailing health but commands total respect in his classroom, preferring a lecture-based approach over student discussion. He introduces his students to heavy philosophical concepts, challenging them to take religious studies seriously.

Jake is Alaska's older boyfriend who currently attends college on a scholarship. He maintains a long-distance relationship with Alaska and represents a serious emotional attachment in her life.

Sara is a Culver Creek student and a Weekday Warrior who dates Chip. Their relationship is highly volatile, characterized by constant squabbling and fundamental disagreements about their respective social circles.

Kevin is a wealthy student at Culver Creek and a prominent member of the Weekday Warriors. He holds a grudge against Chip, believing him responsible for getting other Weekday Warriors expelled, and frequently instigates conflicts.

Marya is Alaska's former roommate who was expelled the previous year after being caught breaking multiple school rules. The mystery of who reported her remains a major topic of speculation among the student body.

Dolores is Chip's mother, a warm and unpretentious woman who lives in a trailer park. She works hard to support her son and shares an exceptionally close bond with him following his father's abandonment.

Miles's mother is an enthusiastic and caring parent who worries about her son's social life. She tries to help him settle into his new school but respects his desire for independence.

Miles's father is a former student of Culver Creek whose past experiences partly inspire Miles to attend the school. He understands the culture of the institution and maintains a bond with his son over their shared alma mater.

Paul is Marya's boyfriend and a Weekday Warrior who was expelled the previous year. His expulsion fuels the ongoing feud between the regular boarders and the weekend students.