Background: Inflammatory bowel diseases (IBDs) have a peak incidence between the second and fourth decades of life and can affect women’s reproductive life. Objectives: Our study aimed to assess the impact of IBD on the reproductive life of female patients with this condition. Design: Cross-sectional study. Methods: Women with IBD followed at our IBD Unit and a group of healthy controls were enrolled. Data on reproductive life were collected using a dedicated questionnaire. Results: The study included 457 women, of whom 228 had IBD, and 229 age-matched healthy controls. No differences were found in the use of contraceptives, infertility, and endometriosis. The risk of spontaneous and voluntary abortions was significantly higher in IBD patients than in healthy controls [odds ratio (OR) 2 and 3.62, respectively]. The risk of obstetrical complications in the IBD population was more than six times higher in patients who experienced disease reactivations during pregnancy than in those with persistent remission [OR 6.9, 95% confidence interval (CI) 1.51–31.28]. Finally, we found that the chances of breastfeeding were 66% lower in patients with IBD than in controls (OR 0.44, 95% CI 0.22–0.91). Conclusion: Our study underlines the negative impact of IBD on women’s reproductive life, supporting the need for proactive preconception counseling.