For this article, a low-cost, compact, and flexible inkjet-printed electromagnetic sensor was investigated for its chemical and biomedical applications. The investigated sensor design was used to estimate variations in the concentration of chemicals (ethanol and methanol) and biochemicals (hydrocortisone—a chemical derivative of cortisol, a biomarker of stress and cardiovascular effects). The proposed design’s sensitivity was further improved by carefully choosing the frequency range (0.5–4 GHz), so that the analyzed samples showed approximately linear variations in their dielectric properties. The dielectric properties were measured using a vector network analyzer (VNA) and an Agilent 85070E Dielectric Probe Kit. The sensor design had a resonant frequency at 2.2 GHz when investigated without samples, and a consistent shift in resonant frequency was observed, with variation in the concentrations of the investigated chemicals. The sensitivity of the designed sensor is decent and is comparable to its non-flexible counterparts. Furthermore, the simulation and measured results were in agreement and were comparable to similar investigated sensor prototypes based on non-flexible Rogers substrates (Rogers RO4003C) and Rogers Droid/RT 5880), demonstrating true potential for chemical, biomedical applications, and healthcare.