(1) Background: This exploratory study aims to explore the relationship between nonspecific chronic spinal pain (nCSP) and insomnia symptoms, by examining the interconnections, strengths, and directional dependence of the symptoms. In addition, we aim to identify the key symptoms of the nCSP–insomnia relationship and shed light on the bidirectional nature of this relationship. (2) Methods: This study is a secondary analysis of the baseline data (cross-sectional) from a randomized controlled trial, which examined the added value of Cognitive Behavioral Therapy for Insomnia (CBT-I) combined with cognition-targeted exercise therapy, conducted in collaboration with the Universiteit Gent and Vrije Universiteit Brussel (Belgium). One hundred and twenty-three nCSP patients with comorbid insomnia were recruited through the participating hospitals, advertisements, announcements in local newspapers, pharmacies, publications from support groups, and primary care. To explore the interconnections and directionality between symptoms and the strengths of the relationships, we estimated a regularized Gaussian graphical model and a directed acyclic graph. (3) Results: We found only one direct, but weak, link between sleep and pain, namely, between average pain and difficulties maintaining sleep. (4) Conclusions: Despite the lack of strong direct links between sleep and pain, pain and sleep seem to be indirectly linked via anxiety and depression symptoms, acting as presumable mediators in the network of nCSP and comorbid insomnia. Furthermore, feeling slowed down and fatigue emerged as terminal nodes, implying their role as consequences of the network.