The flowers of Aloe chortolirioides var. woolliana grow in unbranched, head-like racemes up to 45 cm tall. This variety is more robust, growing taller than var. chortolirioides.

The peduncle is flattened low down, terete (cylindrical) higher up, bearing spaced, papery, sterile bracts below the inflorescence. There are about 18 flowers in the average raceme.

The perianth tubes are about 3,5 cm long, narrow, variably bulging in the centre and pendulous when open. Flower colour is red, but the occasional plant bears yellow, orange or pink flowers. The dark segment tips may become yellowish.

The anthers are exserted, the filaments pale yellow. The olive-green ovary is six-grooved. Flowering time is winter and spring (Craib, 2005; Van Wyk and Smith, 2003; Reynolds, 1974; Jeppe, 1969; iNaturalist).