Aim: This in vitro study aimed to compare the light-transmission properties of two chairside CAD/CAM lithium disilicate (LD) ceramics (a novel fully crystallized and a traditional pre-crystallized) across varying thicknesses. Materials and Methods: One hundred flat specimens were obtained from precrystallized (e.max CAD, Ivoclar Vivadent, Schaan, Liechtenstein) and fully crystallized (LiSi GC Block; GC, Tokyo, Japan) LD at five different thicknesses (0.5, 0.75, 1.0, 1.50 and 2.0 mm). All specimens were polished with a polishing system for lithium disilicate restorations following recommendations from the manufacturer. Light transmission was evaluated with a radiometer. The statistical analysis between e.max CAD and LiSi GC Block was performed using a Mann–Whitney test for each thickness at a significance level of 0.05 (p < 0.05), followed by a Kruskal–Wallis test to compare the light transmission between the thicknesses of e.max CAD and LiSi GC Block. Results: Light transmittance was significantly affected by ceramic thickness. The 0.5 mm thick specimens exhibited the highest transmittance values compared to all other groups, while a light transmittance of 0.00 was observed in the 2.0 mm thick specimens for both e.max CAD and LiSi GC Block. In the comparison between e.max CAD and LiSi GC Block according to thickness, there was a statistically significant difference exclusively between groups with a thickness of 1.50 mm (p = 0.002). Conclusions: Light transmission for pre- and fully crystallized CAD/CAM lithium disilicate ceramics only showed a statistical difference at the thickness of 1.50 mm (p = 0.002). E.max CAD demonstrated acceptable light transmission up to a thickness of 1.5 mm. Clinical Significance: A thickness of 2 mm for chairside CAD/CAM lithium disilicate ceramics, whether pre-crystallized or fully crystallized, necessitates the use of dual-cure resin luting cement due to reduced light transmission.