If you loved Detective Conan: Jolly Roger in the Deep Azure, try Detective Conan: Magician of the Silver Sky
A bridge between a film you've already seen and one most people haven't. Here's what they share, and what the second one does that the first one doesn't.

Detective Conan: Jolly Roger in the Deep Azure

Detective Conan: Magician of the Silver Sky
What they share
Both films are directed by Yasuichiro Yamamoto, and they both carry the playful mood tag, and they sit in Adventure / Animation territory. If that's the register that drew you to Detective Conan: Jolly Roger in the Deep Azure, the second film will land in a comparable space — through a different lens.
What Detective Conan: Magician of the Silver Sky is
Hakodate. Winter wind. A playing card pinned to the door. A famous actress asks a sleepy detective to guard her sapphire, but Conan suspects a trap when the Kaitou Kid announces his arrival on a passenger jet. A locked-room mystery at 30,000 feet. One of the more playful entries in the long-running anime series.