Background: Urinary tract infections (UTIs) are one of the most common bacterial infections during pregnancy, posing significant risks to maternal and perinatal health. Pregnant women are more susceptible to UTIs due to anatomical and physiological changes, including ureteral dilation and urinary stasis. Inadequate management can lead to complications such as pyelonephritis, preterm labor, and low birth weight. Understanding the risk factors and outcomes of UTIs is crucial for improving maternal and neonatal health, particularly in resource-limited settings like Bangladesh. Objective: To identify the risk factors of UTIs among pregnant women and assess their maternal and perinatal outcomes. Methodology: A case-control study was conducted at a tertiary medical college and hospital in Bangladesh from January 2022 to January 2023. Pregnant women aged 13–26 weeks with culture-positive UTIs were included as cases, and age-matched women with negative urine cultures served as controls. A total of 250 participants were enrolled. Data on socio-demographic variables, clinical symptoms, and pregnancy outcomes were collected using structured questionnaires. Statistical analyses were performed to explore associations between risk factors and UTI occurrence. Results: The prevalence of mid-trimester UTIs was 12.30%. The majority of cases (40.5%) were in the 20–30 age group. Escherichia coli (E. coli) was the most common causative organism, followed by Pseudomonas and Klebsiella. Risk factors included a history of UTI during the current pregnancy (22%) and increased sexual activity during early pregnancy (34.7%). Asymptomatic bacteriuria was the most frequent condition observed (32.3%). Maternal outcomes included a higher rate of caesarean delivery and preterm labor, while perinatal outcomes showed significantly lower birth weights in infants born to mothers with UTIs. Conclusion: UTIs in pregnancy are associated with significant maternal and perinatal risks, including preterm labor and low birth weight. Routine screening and early intervention can reduce complications. Efforts to improve awareness, prenatal care, and access to healthcare are essential for addressing UTIs in pregnant women, particularly in resource-limited settings.