Surface engineering can be used to prevent ice accumulation and adhesion in environments that deal with icing problems. One recent engineering approach, slippery liquid infused porous surfaces (SLIPS), comprises a smooth and slippery lubricating surface, where lubricant is trapped within the pores of a solid material to repel various substances, such as water and ice. However, it remains unclear whether the slippery surfaces retain their icephobic characteristics under the impact of supercooled water droplets or repeated freezing and melting cycles. Here, the icephobic properties of SLIPS are evaluated under multiple droplet freeze–thaw and ice accretion–detachment cycles and compared to hydrophobic and superhydrophobic surfaces. The experiments are designed to mimic real environmental conditions, thus, the icephobicity is investigated in icing wind tunnel, where ice accretion occurs through the impact of supercooled water droplets. The adhesion of ice remained extremely low, <10 kPa, which is four times lower than ice adhesion onto smooth fluoropolymer surfaces, even after repeated ice accretion–detachment cycles. Moreover, cyclic droplet freeze–thaw experiments provide insight into the effects of temperature cycling on SLIPS wettability, showing stable wetting performance. The results suggest liquid infused porous surfaces as a potential solution to icephobicity under challenging and variating environmental conditions.