Modern aero-engine combustion chambers burn a lean and premixed mixture, generating a turbulent flame which involves large heat-release fluctuations, thus producing unsteady temperature phenomena commonly referred to as entropy waves (EWs). Furthermore, to enhance the fuel air mixing, combustion air is swirled, leading to vorticity disturbances. These instabilities represent one of the biggest challenges in gas turbine design. In this paper, the design and testing of a novel entropy wave generator (EWG) equipped with a swirler generator (SG) are described. The novel EWG will be used in future works on the high-speed test rig at Politecnico di Milano to study the combustor–turbine interaction. The paper shows the process of the EWG geometry and layout. The EWG is able to produce an engine-representative EW, the extreme condition is at the maximum frequency of 110 Hz, a peak-to-valley temperature value of 20 °C and swirling angles of ±25° are measured. By virtue of these results, the proposed system outperforms other EWG devices documented in the literature. Furthermore, the addition of a swirling generator makes this device one of a kind.