Pain in sickle cell disease (SCD) is often associated with increased morbidity, mortality, and high healthcare costs. The standard method for predicting the absence, presence, and intensity of pain has long been self-report. However, medical providers struggle to manage patients based on subjective pain reports correctly and pain medications often lead to further difficulties in patient communication as they may cause sedation and sleepiness. Recent studies have shown that objective physiological measures can predict subjective self-reported pain scores for inpatient visits using machine learning (ML) techniques. In this study, we evaluate the generalizability of ML techniques to data collected from 50 patients over an extended period across three types of hospital visits (i.e., inpatient, outpatient and outpatient evaluation). We compare five classification algorithms for various pain intensity levels at both intra-individual (within each patient) and inter-individual (between patients) level. While all the tested classifiers perform much better than chance, a Decision Tree (DT) model performs best at predicting pain on an 11-point severity scale (from 0–10) with an accuracy of 0.728 at an inter-individual level and 0.653 at an intra-individual level. The accuracy of DT significantly improves to 0.941 on a 2-point rating scale (i.e., no/mild pain: 0–5, severe pain: 6–10) at an inter-individual level. Our experimental results demonstrate that ML techniques can provide an objective and quantitative evaluation of pain intensity levels for all three types of hospital visits.