(1) Background: Midline meningiomas such as olfactory groove (OGMs), planum sphenoidale (PSMs), or tuberculum sellae meningiomas (TSMs) are challenging, and determining the appropriate approach is important. We propose a decision algorithm for choosing suitable transcranial approaches. (2) Methods: A retrospective chart review between 06/2007 and 01/2020. Clinical outcomes, radiographic findings, and postoperative complication rates were analyzed with respect to operative approaches. (3) Results: We included 88 patients in the analysis. Of these, 18.2% (16/88) underwent an interhemispheric approach, 72.7% (64/88) underwent a pterional/frontolateral/supraorbital approach, 2.3% (2/88) underwent a unilateral subfrontal approach, and 6.8% (6/88) underwent a bifrontal approach. All OGMs underwent median approaches, along with one PSM. All of the other PSMs and TSMs were resected via lateral approaches. The preoperative tumor volume was ∅ 20.2 ± 27.1 cm3. Median approaches had significantly higher tumor volume but also higher rates of Simpson I resection (75.0% vs. 34.4%). An improvement of visual deficits was observed in 34.1% (30/88). The adverse event rate was 17.0%. Median follow-up was 15.5 months (range 0-112 months). (4) Conclusions: Median approaches provides satisfying results for OGMs, lateral approaches enable sufficient exposure of the visual apparatus for PSMs and TSMs. In proposing a simple decision-making algorithm, the authors found that satisfactory outcomes can be achieved for midline meningiomas.