Insects behaviorally thermoregulate across the diel cycle and their preferred microhabitats change based on current resource availabilities and the thermal performance optima of traits. Specific combinations of traits being prioritized are set by life history strategies, making life history an important intrinsic determinant of thermal preferences. However, we do not know how life history strategies shape plasticity of behavioral thermoregulation, limiting our ability to predict responses to environmental variability. We compared female variable field crickets (Gryllus lineaticeps) that are flight-capable (long-winged) and flightless (short-winged) to test the hypothesis that life history strategy determines plasticity of thermal preferences across the diel cycle and following starvation. Thermal preferences were elevated during the nocturnal activity period, and long-winged crickets preferred warmer temperatures compared to short-winged crickets across the diel cycle when fully fed. However, thermal preferences of starved crickets were reduced compared to fed crickets. The reduction in thermal preferences was greater in long-winged crickets, resulting in similar thermal preferences between starved long- and short-winged individuals and reflecting a more plastic response. Thus, life history does determine plasticity in thermoregulatory behaviors following resource limitations and effects of life history on thermal preferences are context dependent.