Chronic diseases are potential risk factors for pregnancy duration and neonatal outcomes. This narrative review aimed to summarize the research results on the specifics of pregnancy in women with obesity and after bariatric surgery. PubMed and Google Scholar databases were searched. Systematic reviews, meta-analyses, clinical trials, and references to identified articles from the last ten years (2013–2023) were included. Ultimately, 107 literature items were qualified. It has been shown that women with obesity planning pregnancy should reduce their body weight because obesity is a risk factor for adverse obstetric and neonatal outcomes. Bariatric surgery effectively reduces excessive body weight and the health risks in women with obesity during pregnancy and their offspring. However, at least a year interval between surgery and conception is recommended. An interdisciplinary medical team should provide patient care during pregnancy with knowledge and skills related to people after bariatric surgery. Due to the increased risk of mental disorders, especially depression, it is necessary to constantly monitor the mental state of women and provide psychological support and education on a healthy lifestyle during pregnancy and the postpartum period.