Vegetable flavour is a quality characteristic for consumer acceptability. Sun and air are traditionally used for drying tomatoes; however, the optimal combination of techniques such as osmotic dehydration or microwave-assisted air-drying could lead to high quality self-stable products. The aim of this paper was to study the influence of different process variables on the volatile profile of dehydrated cherry tomato halves. The analysed variables were: air-drying temperature (40 and 55 °C), microwave power (0 and 1 W/g) and previous osmotic dehydration with a 55 Brix binary sucrose solution at 30 °C for 120 min (OD1) or ternary solution of 27.5% sucrose + 10% NaCl (w/w) at 40 °C for 60 min (OD2). Twenty major volatile compounds were identified in fresh tomatoes. Among them, 2-isobutylthiazole and 6-methyl-5-hepten-2-one stand out as impact volatile compounds. Dehydration modified the volatile profile, mainly due to the changes induced in some typical fresh-like tomato compounds, but also due to the generation of five new compounds: 1-butanol, 2-methyl-2-butenal, 3-hydroxy-2-butanone, furfural, acetonitrile, related to Maillard reactions, and the catabolism of carotenoids and polyunsaturated fatty acids. Principal component analysis showed the possibility of obtaining dried cherry tomatoes with different volatile profiles, depending on drying conditions.