Background: Under Title IX, pregnant and/or parenting students (PPY) are protected from discrimination and are required to receive equal access to education. This study examines the implementation of Title IX, investigating whether Title IX rights are upheld for pregnant and/or parenting students attending Chicago Public Schools (CPS) using qualitative research methods. Methods: Stakeholder interviews with pregnant and/or parenting students and staff members at CPS were conducted. Qualitative data were transcribed, and a codebook was developed of common key themes. Results: Results indicated Title IX is not implemented to its fullest extent or consistently throughout CPS. Pregnant and parenting students experienced a range of academic environments from supportive to hostile. Some students lacked accommodations and academic planning. Conclusion: Study findings can inform policymakers in improving Title IX policy and guide schools on compliance with Title IX. Schools must aim to act beyond policy to meet the needs of pregnant and parenting students and ensure their future success.