Background: Intrahepatic cholestasis of pregnancy (ICP) and hyperemesis gravidarum (HEG) are pregnancy-specific liver diseases associated with significant fetal and maternal complications. Typically, HEG is diagnosed in the first trimester of pregnancy, and ICP in the third trimester of pregnancy. The aim of this study is to investigate whether primigravid women diagnosed with ICP between the 26th and 37th weeks of pregnancy were also diagnosed with HEG during the first trimester, and to evaluate whether the diagnosis of ICP can be predicted in pregnant women with a prior diagnosis of HEG. Methods: Our study is a retrospective analysis. A total of 4000 pregnant women, aged 18 to 45 years and between 26th and 37th weeks of gestation, who presented to the Gynecology and Obstetrics Clinic of the Health Sciences University, Istanbul Training and Research Hospital with complaints of pruritus between 01/07/2018 and 01/07/2023, were screened. 227 patients were diagnosed with ICP. Complete medical records and blood test results were available for 141 patients. 39 patients with a history of previous pregnancies and/or comorbidities, as well as 30 patients without available serum total bile acids (TBA) results, were excluded from the study. Of these, 72 pregnant women who met the inclusion criteria were enrolled in the study and grouped into primigravid women with and without a history of HEG in the first-trimester. Demographic characteristics, gestational age, detailed medical history, ultrasound findings, and biochemical parameters—including alanine aminotransferase (ALT), aspartate aminotransferase (AST), albumin, bilirubin, and fasting bile acid (FBA) levels were statistically compared. Results: In our study, comparisons revealed no significant differences in AST, ALT, alkaline phosphatase (ALP), gamma-glutamyl transferase (GGT), and direct bilirubin levels (p > 0.05) between the groups with and without a history of HEG diagnosed with cholestasis. In pregnant women diagnosed with cholestasis, the total bilirubin and indirect bilirubin levels were significantly lower (p < 0.05) in the group with a history of HEG compared to the group without a history of HEG. In contrast, TBA levels were significantly higher (p < 0.05) in the group with a history of HEG compared to the group without a history of HEG. Conclusions: This study found that primigravid women with ICP and a history of HEG had elevated TBA levels, while total and indirect bilirubin levels were reduced. This suggests that patients with a history of HEG should be closely monitored in later stages of pregnancy for the development of ICP and potential liver damage. However, larger and more comprehensive studies are needed to confirm these findings.