Background: The escalating prevalence of obesity in women of reproductive age raises concerns about its impact on maternal and fetal health during pregnancy. This study aimed to thoroughly assess how obesity affects pregnancy and neonatal outcomes among Saudi pregnant women. Methods: In a retrospective cross-sectional study, we analyzed 8426 pregnant women who delivered at King Fahad National Guard Hospital in Riyadh in 2021. Of these, 3416 had obesity, and 341 of them, meeting the inclusion criteria, were selected. Maternal and neonatal outcomes were compiled using a structured questionnaire and extracted from the hospital’s “Best Care” data-based registration system. Results: The findings highlighted that 40.5% of pregnant women were classified as obese, with almost half falling into obesity class II based on BMI. Obesity correlated significantly with adverse maternal outcomes like gestational diabetes and increased rates of cesarean deliveries. Additionally, maternal obesity was linked to unfavorable fetal outcomes, including higher rates of newborn intensive care unit admissions, lower APGAR scores at 1 min, and a greater likelihood of macrosomia. Conclusions: This study underscores the important impact of maternal obesity on both maternal and fetal health during pregnancy. Addressing this high-risk condition demands targeted educational programs for women of reproductive age focusing on BMI control, dietary adjustments, and lifestyle modifications to mitigate obesity-related complications during pregnancy.