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Inflammatory myofibroblastic tumors (IMTs) are rare mesenchymal neoplasms with intermediate malignant potential. While most commonly arising in the lung, airway involvement is exceedingly uncommon. Endobronchial IMTs typically manifest with symptoms of airway obstruction, including dyspnea, wheezing, and stridor. Diagnosis involves radiological imaging, bronchoscopic evaluation, and histopathological analysis. Additionally, assessment of anaplastic lymphoma kinase (ALK) status is particularly important in young and pediatric patients, as ALK-targeted therapies constitute a viable treatment option for tumors harboring ALK rearrangements or other actionable kinase fusions. Complete surgical resection remains the gold standard for treatment; however, bronchoscopic resection may be an effective option in selected cases. Herein, we describe two cases of IMTs involving the airways-one in an adult and one in a child-both presenting with significant airway obstruction and managed with bronchoscopic resection.