Kit Cloudkicker steals a treasure from Don Karnage, which puts Karnage and his pirates on the boy's trail. Meanwhile, Baloo takes Kit to Cape Suzette, where they take on a job to deliver gorilla birds to raise the money needed to save Baloo's trusty plane from being foreclosed.
Before Baloo can pay off his plane, a woman named Rebecca Cunningham shows up as the new owner of his business. This rings in change, as Baloo's Air Service becomes Higher for Hire and the new home of Rebecca and her young daughter Molly. In the process of tracking down Kit's stolen jewel, Baloo and Kit fend off pirates and meet with Shere Khan.
Baloo feels threatened when a prestigious professor comes to town touting a mechanical pilot. He agrees to a bear vs. robot race, with the stakes high and many a fate resting on his performance; a loss could just single-handedly change the face of aviation!
Kit's debut babysitting of Molly becomes even more challenging when two of Don Karnage's pirates make an unprecedented entry into Cape Suzette and a giant squid is unleashed.
When Baloo loses a $10,000 piece of cargo, he tries to make things right with the client -- a hoodlum alligator with two thick henchmen -- while letting Wildcat oversee his travel tour.
Rebecca's demanding workday enables Molly to wander off with Henry, a baby "buffalo" she discovers. The critter, it turns out, is actually a dragon-like animal who can magically shrink and grow at will. While Kit and Molly try to reunite Henry with his mother, the hunter who bagged the creature tries to reclaim him.
When Baloo has his pilot's license temporarily revoked, Rebecca buys a book and tries to teach herself to fly. Her efforts lead the gang to an icy place where they are taken prisoner by Don Karnage.
A crook named Mr. Covington, whose priceless doll has ended up in the hands of Molly, puts on precisely the sophisticated air that Rebecca has been looking for in order to reclaim his stolen loot.
Higher for Hire goes into the skywriting business, which underscores the importance of spelling for Baloo and Kit. Unfortunately, it also leads to the gang unwittingly aiding criminal activity.
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