I mean it’s no different from travelling to Yavin IV from the Death Star. It’s always been a bit whimsical. I’d say the worse offenders are the Sequels. Namely J.J.'s films.
The Falcon got to Bespin I think with clever skill on Han’s part as he followed along to Imperial standards of dumping garbage before they make their jump to Hyperspace. He just didn’t expect Boba to catch on. Boba learned from a very similar experience with Obi-Wan when with Jango in the asteroid field.