Chaotic optical communication has shown large potential as a hardware encryption method in the physical layer. As an important figure of merit, the bit rate–distance product of chaotic optical communication has been continually improved to 30 Gb/s × 340 km, but it is still far from the requirement for a deployed optical fiber communication system, which is beyond 100 Gb/s × 1000 km. A chaotic carrier can be considered as an analog signal and suffers from fiber channel impairments, limiting the transmission distance of high-speed chaotic optical communications. To break the limit, we propose and experimentally demonstrate a pilot-based digital signal processing scheme for coherent chaotic optical communication combined with deep-learning-based chaotic synchronization. Both transmission impairment recovery and chaotic synchronization are realized in the digital domain. The frequency offset of the lasers is accurately estimated and compensated by determining the location of the pilot tone in the frequency domain, and the equalization and phase noise compensation are jointly performed by the least mean square algorithm through the time domain pilot symbols. Using the proposed method, 100 Gb/s chaotically encrypted quadrature phase-shift keying (QPSK) signal over 800 km single-mode fiber (SMF) transmission is experimentally demonstrated. In order to enhance security, 40 Gb/s real-time chaotically encrypted QPSK signal over 800 km SMF transmission is realized by inserting pilot symbols and tone in a field-programmable gate array. This method provides a feasible approach to promote the practical application of chaotic optical communications and guarantees the high security of chaotic encryption.