Baloo enters a race against a robot pilot to prove that a good old fashioned pilot is better than a machine. The catch: If he fails, all of the pilots in Cape Suzette will be out of work.
Kit is anxious to tackle his first baby-sitting job and promises Rebecca that her daughter Molly is safe with him. But Kit has to learn that the little girl turns out to be quite a handful.
When Baloo is late one too many times, Rebecca makes him fly a guided tour, going past certain checkpoints at designated times. However, Baloo hears of a stolen crown and concocts a scheme to get it back while Wildcat flies the tour.
Molly becomes a surrogate mother to a flying creature that becomes large when it gets wet and small when it dries. This becomes more difficult when she has to protect the creature from the bloodthirsty poacher MacKnee.
Rebecca takes over flying the Sea Duck after Baloo's license is temporarily suspended while trying to evade air pirates. The move causes havoc as Higher for Hire attempts to deliver a block of ice to a wealthy desert prince.
Covington, a notorious jewel thief, hides a valuable item in the Sea Duck. When he tries to retrieve it, he discovers that Baloo and Kit have cleaned out the plane and Molly has added the item to her doll collection.
Kit befriends a parrot, Ignatz, who claims to know about some buried treasure. Baloo meanwhile is upset when Rebecca charges him for the value of a shipment of expensive crystal, which was actually broken by air pirates.
Baloo's bad spelling hampers Rebecca's attempt to go into the skywriting business. Meanwhile, a notorious criminal uses the skywriting to attempt to send coded messages to his henchmen and hold Cape Suzette for ransom.
After Kit gets into an argument with Baloo about taking unnecessary risks, he runs away to join an air circus led by Daring Dan Dawson. However, Dawson makes Kit perform even more dangerous stunts, and it is up to Baloo to rescue Kit.
Rebecca misinterprets a phone call as news that Baloo is dying. When Baloo finds out, he decides to fly to the Bearmuda Trapezoid, from which no pilot has ever returned.
When a debonair ghost ship captain sweeps Rebecca off her feet, she enjoys what she thinks is a dream. When Baloo and Louie decide to exorcise the ghost, Rebecca is forced to choose between her dream and her daughter.
Baloo and Kit find a whale and turn it in for the reward. Later they find out the poor conditions the whale is forced to be in and decide to set him free.
Colonel Spigot is charged with presenting a golden sprocket as a gift to the Mayor of Cape Suzette, but Trader Moe wants to steal the sprocket, and it is up to Kit and Baloo to stop him and help Spigot.
Rebecca starts a midair refueling station, which is a hit with the pilots and boosts business. Trouble is, it significantly lowers business for Louie, who starts his own rival station to compete, and Baloo and Kit are caught in the middle.
Planes and pilots and are mysteriously going missing. So Shere Kahn dupes the dimwitted Baloo and his sidekick Kit Cloudkicker to go on a dangerous mission as his decoys.
Baloo and Kit are captured by Don Karnage and his gang of pirates. Baloo, however, is severely down in the dumps and out of confidence because of him crashing the Sea Duck into the ocean. It is up to Kit to get them to escape.
Baloo lets his pilot's license expire, but has trouble renewing it when his examiner rattles him by requiring him to perform his actions alphabetically. He then learns that Don Karnage has teamed up with Shere Khan.
Baloo is starstruck when he meets film star Kitten Kaboodle, and immediately signs on as her stunt pilot. Concerned for Baloo as his friend, Rebecca learns that the "accidents" on Kitten's set are no accidents.
Wanting to cater to only the upper class, Rebecca puts up the Sea Duck as collateral insurance. However, Baloo loses the shipment - and the Sea Duck - to what turn out to be two con artists posing as a wealthy couple.
Baloo is upset when Rebecca gets a truffle-hunting pig instead of a new pontoon. Refusing to believe that her idea may not be good, Rebecca gets herself and the pig enslaved by pygmies, and it is up to Kit and Baloo to save her.
Baloo learns he's actually a long-lost baron, but when he goes to the mansion that he has supposedly inherited, there are several attempts on his life.
A magical idol switches Baloo with Kit and Rebecca with Don Karnage. They are then involved in a race against time to get back to normal; if they fail, by sunrise they will remain like this forever.
Legendary hero Whistlestop Jackson pays a visit to Cape Suzette and volunteers to do a special cargo run for Higher for Hire, but Shere Khan, his longtime rival, has other plans.
When Baloo learns that Kit's life savings will pay for him to replace his favorite record, he offers to double Kit's money if Kit lets him "invest" it.
Higher for Hire's business is suffering because its boss is female. Baloo decides to enter an air scavenger hunt, but only an all-female aviation club will sponsor Higher for Hire, so he disguises himself as a lady to do so.
Baloo finds the legendary "Panda-La", a mystical place, where he is warmly received. The reception, however, turns out to be a ruse, as Panda-La's inhabitants decide to attack Cape Suzette.
When Wildcat babysits Molly, she convinces him to take her to Thembria to see snow. Once there, however, they have fun, which gets them imprisoned because having fun is illegal in Thembria.
Baloo suffers amnesia after he hits his head while taking a shortcut during a cargo run. He then lands on an island where an old pilot, Joe McGee, helps him remember how to fly.
Rebecca overworks Baloo to the point where he lies to her to get some time off. The lie escalates into a Martian invasion, which quickly becomes complicated when a trigger-happy colonel overhears the conversation over the radio.
Kit introduces his friend, accident-prone Oscar Vandersnoot, to his club, but Oscar needs an adventure to join. When Kit decides to get Oscar his adventure, he gets more than what he bargained for when Don Karnage kidnaps Oscar for ransom.
When orphan Kit Cloudkicker steals a gem-like treasure from Don Karnage and his air pirates, he is chased to Louie's Island where he meets Baloo the Bear, a carefree cargo pilot.
Kit and Baloo decide to rescue Rebecca and Molly from the air pirates. But while sneaking into the lair, they discover Don Karnage's plan to use the gem for a "lightning gun."
Still smarting from Kit's presumed betrayal, Baloo quits his job and flies away. Meanwhile, Don Karnage attacks Cape Suzette with his lightning gun, destroying all their defenses.
Baloo makes Rebecca think it is one day later than it actually is so he can get paid early. That one day, however, turns out to be significant as Rebecca then claims that Baloo missed important deliveries. The conflict quickly escalates.
Vacationing Baloo and Louie swear off women and crazy treasure hunts. Then they meet Katie the archeologist in distress. They help protect her from villains as she searches for a buried lost city.
Baloo and company visit one of Shere Khan's mining operations, which is overseen by a sheriff who mistreats the workers. When the workers mistake Wildcat for Khan, they kidnap him, but Khan learns of the abduction and goes to investigate.
When Baloo learns that all that Molly wants for Christmas is for it to snow for her mom, he takes Kit and Rebecca on a mission to make Molly's wish come true.
Rebecca decides to shmooze with the upper class by booking a reservation on the "Spruce Moose". Trouble is, Baloo's crude, unrefined behavior causes problems, but he then has to save the day when the Spruce Moose is hijacked.
When Baloo delivers a package to Walla Walla Bing Bang, he runs into an old rival, Airplane Jane, and a battle for Walla Walla Bing Bang's throne between Princess Grace and her long lost cousin Prince Rudolf.
When Kit, who yearns to be a pilot even though he's too young, hears that the flying age has been lowered to twelve in Thembria, he goes there - only to discover that the whole thing is just a ruse and the kids won't actually be flying.
A case of mistaken identity causes what would have been a routine prisoner transport to become a serious headache for Baloo as he is pursued by both gangsters and the cops.
When a mishap during a delivery knocks out the sentries who man Cape Suzette's cliff guns, Baloo and an old codger, who hasn't fired the guns in years, are forced to man the guns to stop Don Karnage and his gang from attacking.
When Baloo and Wildcat deliver an Egyptian tablet to an archaeologist who plans to open her own museum, the delivery becomes anything but routine as they look for a lost treasure and try to evade air pirates, traps and an ancient guardian.
