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In the eclectic city of Cleveland, Ohio, high school senior Karen "Wren" DeSantis (Karen) paints a vivid picture of Halloween in her hometown - a time when residents shed their inhibitions and embrace their quirks. Wren's widowed mother, Joy, has recently found love with the much-younger Keevin, while Wren herself is fixated on the promise of college life at New York University. Her friend April covets social status, and Roosevelt, her bookish companion, harbors a secret crush on Wren.

As Halloween approaches, the two friends are thrilled to receive an invitation to a party hosted by local heartthrob Aaron Riley (Aaron Riley). However, their excitement is short-lived, as Wren's mother commands her to take her 8-year-old brother Albert trick-or-treating instead, so she can attend a party with Keevin. The evening takes an unexpected turn when Joy finds herself at a gathering orchestrated by Keevin's friend Nate Brueder.

Meanwhile, Wren and April find themselves at a haunted house, where they reunite with Roosevelt and his best friend Peng. In the chaos that ensues, Albert goes missing, only to stumble upon Fuzzy, a convenience store employee seeking revenge against Jörgen, a mixed-martial arts fighter who won over Fuzzy's ex-girlfriend Lara.

As Wren desperately searches for her brother, she implores Roosevelt to ask his parents - two semi-eccentric pacifistic lesbians - to lend their Volvo. When they refuse, he takes matters into his own hands and borrows the car without permission.

The trio's quest to find Albert takes them on a wild goose chase across town, with Wren suspecting that her brother might be hiding at Captain Chicken, a fictional pirate-themed fast food chain on Euclid Avenue. Despite narrowly missing him, they're forced to flee from local bully Mike Puglio, only to have Albert rescued by Denise, a college girl dressed as the enigmatic "Galaxy Scout" (a fictional anime character).

As Roosevelt's reckless driving causes chaos at Captain Chicken, April makes her escape, and Wren is left to frantically search for her brother. After being accosted and robbed of his candy by Jörgen at Denise's party, Albert stows away in the mixed-martial artist's convertible.

With Wren, Roosevelt, and Peng hot on their trail, they set out to find both Albert and April, who has mistakenly reported finding their friend at Aaron Riley's party. Upon arrival, they're met with the earlier showdown between Puglio and Peng, which surprisingly brings the latter some social acceptance.

As Wren's world begins to unravel, she receives an ominous phone call from Jörgen, who has taken Albert hostage at his residence. The captor demands a ransom of $400 in cash, a sum that Wren desperately scrambles to gather. Jörgen taunts her with the threat of turning them over to the authorities if his demand is not met. With time running out, Wren frantically navigates the streets of Cleveland, driven by a sense of desperation as she searches for Jörgen's address.

Upon arriving at the house, Wren pleads with Jörgen, explaining that she has no money to offer. In a surprising twist, Jörgen reveals his fondness for the Beastie Boys, and Wren seizes upon this shared interest to negotiate an alternative. She offers him her late father's rare collectible jacket, passed down from Mike D himself, as a substitute for the cash. The prospect of owning such a valuable item seems to pique Jörgen's interest.

However, just as it appears that Wren has brokered a deal, Fuzzy bursts into the scene, armed with fireworks designed to distract and disorient Jörgen. In the ensuing chaos, Albert is rescued, and Jörgen suffers a nasty injury from the explosive detonation.

As the dust settles, Wren and Albert pay a poignant visit to their father's grave at the local cemetery, leaving behind a symbol of hope - a plastic pumpkin adorned with flowers. It is here that Albert expresses his gratitude to Wren for her bravery in rescuing him. The siblings' mother soon arrives, and the trio departs for home.

Meanwhile, Roosevelt makes amends for his earlier mischief by committing to a part-time job at Captain Chicken to cover the damages he caused. With his conscience clear, he confesses his feelings to Wren, paving the way for a romantic interlude. As the evening unfolds, April finds herself in Peng's arms once more, deciding to indulge in another passionate moment with her suitor.

In a separate development, Fuzzy meets Denise and is asked out on a date. He also reveals his true identity as Manuel. Later, Albert's mischievous streak is exposed when he confesses that he has been orchestrating prank phone calls for six months, targeting his mother, sister, and even Wren herself. The extent of his antics is revealed to include uploading a video to Wren's Facebook page, mocking her bug dance and "explaining rap."