The Dark Web sites are operated over anonymity-preserving protocols like Tor, making users of the Dark Web services more resilient to identification and monitoring. Although some previous works have focused on understanding the size of the Dark Web services and investigating their criminal activities, there is a lack of research on chronological analysis and in-depth profiling of the Dark Web sites, particularly in South Korea. Therefore, in this study, we implemented a Dark Web crawling system, and collected seed and sub Dark Web URLs using it. Then, the 3,000 Dark Web sites from the seed URLs were selected and their web pages were captured for profiling. An in-depth analysis was then conducted on the collected 3,000 Dark Web sites, and an intensive categorization was performed on the basis of their major criminal activities. We then carried out an in-depth profiling for top 3 Korean Dark Web sites to investigate cyber criminal activities in South Korea. In the profiling, criminal activities were collected and analyzed in a chronological point of view. Personal information leakage and Sybil IDs in the Dark Web were also identified based on the PGP keys we collected.