In order to find a short, economically feasible process for chalcopyrite preconcentration and to provide a reference for the preconcentration of similar copper sulfide ores, the particle size characteristics of the crushed products from a high-pressure grinding roller (HPGR) and jaw crusher (JC) were analyzed, as well as the liberation degree and fracture characteristics of the chalcopyrite. The float–sink test (FST) was carried out on the crushed products, and the effects of the two crushing methods on the FSTs of the crushed products were compared. The research results show that at the same crushing fineness, the chalcopyrite liberation in HPGR products can be enhanced by 14%~18% compared with the JC. The single-particle crushing of the JC tends to produce intergranular fracturing of chalcopyrite, while the lamination crushing of the HPGR produces more transgranular fracturing of chalcopyrite; the chalcopyrite in the −5 + 0.5 mm size fraction mainly produces intergranular fracturing, and the chalcopyrite in the −0.5 mm size fraction mainly produces transgranular fracturing. The FST results show that heavy media preconcentration was suitable for chalcopyrite, and, in the optimal conditions of a size fraction of −3 + 0.5 mm and separation density of 2.55 g/cm³, the grade and distribution rate of Cu in the sinks obtained by HPGR-FST were 0.35% and 89.86%, respectively, and the floats yield was 24.76%, with a better enrichment of sinks and higher floats yields, which was better when compared with that of the JC-FST.