(1) Background: Gastroretentive systems are an interesting option for enhancing the bioavailability of weak bases and poorly soluble drugs. The aim of this study was to formulate supramolecular organogels based on cinnarizine (CIN) as a potential gastroretentive system. (2) Methods: The organogels were prepared with different oils in different ratios. Thereafter, their pharmaceutical characteristics and in vitro gastric retention were evaluated through in vitro and in silico simulations. (3) Results: Organogels with different proportions of CIN to oils were successfully obtained. The DSC thermal analysis results demonstrated that all organogels showed gel–sol temperature transitions. The frequency sweep test verified that all organogels presented frequency-independent behavior. Optical imaging revealed longitudinal spherulites of the 1:4 CIN in organogels in all oils. The CIN organogels in all oils (1:4) were observed to float in gastric media during the entire release study. The pharmacokinetic parameters of CIN in peppermint oil (1:4) revealed a close Cmax value to that of the 25 mg immediate-release tablet, but a different AUC. (4) Conclusions: The organogels in all oils floated throughout the release study, establishing their potential as a gastroretentive system. Furthermore, these dosage forms were assessed as a gastric-controlled system through in silico simulations, which enabled prediction of their pharmacokinetic parameters.