An instrumentation system for in-situ measurement of the inner-outer pressure differential at the upper and lower surfaces of dynamically inflatable wings is designed and tested, revealing important insights into the aerodynamic characteristics of inflatable airfoils. Wind tunnel tests demonstrated full capability of low-pressure differential readings in the range of 1.0–120 Pa, covering speeds from 3 to 10 m/s at angles of attack from −20 to +25°. Readings were stable, presenting coefficients of variation from 2% to 7% over the operational flight envelope. The experimental data confirmed the occurrence of a bottom leading-edge recirculation bubble, linked to the low Reynolds regime and the presence of an air intake. It supported the proposition of a novel approach to aerodynamic characterization based on local pressure differentials, which takes in account the confined airflow structure and provides lift forces estimations compatible with practical observation. The results were also compatible with data previously obtained following different strategies and were shown to be effective for parameterizing the inflation and stall phenomena. Overall, the instrumentation may be applied straightforwardly as a flight-test equipment, and it can be further converted into collapse alert and prevention systems.