Background: The rising incidence of hypertension (HTN) in pediatric patients imposes the need for its timely recognition by finding the optimal screening population. The goal of our study was to explore the ambulatory blood pressure (BP) parameters in selected groups of obese children and adolescents with different obesity levels and quantify the impact of parental hypertension (PH) on their blood pressure (BP) values. Methods: This retrospective study included 176 obese Caucasian patients, 94 (53.4%) males, aged 6-18 years, who were divided based on their office blood pressure (OBP), body mass index (BMI) Z-score, and history of PH. Results: Patients with PH had a significantly higher prevalence of masked hypertension (MH) and higher BMI (p=0.007 and p<0.001, respectively) compared to those with normotensive parents. There was no difference in whether HTN was of maternal or paternal origin, although the subjects with both hypertensive parents had higher diastolic blood pressure (DBP) parameters: office DBP (p=0.013), 24-hour DBP (p=0.017), and nighttime DBP (p=0.002). The multivariate regression analysis identified office systolic blood pressure (SBP) as a significant overall predictor of HTN (p<0.001), including the group with normotensive parents. In contrast, resting heart rate (HR) was an important predictor of HTN in subjects with PH (p=0.002). Additionally, a non-dipping BP pattern was predominantly observed in obese subjects, regardless of the degree of obesity (p=0.587). Conclusion: Our results emphasize the importance of performing ambulatory blood pressure monitoring (ABPM) in obese children and adolescents, especially those with a history of PH. This group represents the target screening population for MH, which increases cardiovascular risk in this population when combined with obesity.