In adapting US agriculture to the climate of the 21st century, a key unknown is whether cropping frequency may increase, helping to offset projected negative yield impacts in major production regions. Combining daily weather data and crop phenology models, we find that cultivated area in the US suited to dryland winter wheat–soybeans, the most common double crop (DC) system, increased by up to 28% from 1988 to 2012. Changes in the observed distribution of DC area over the same period agree well with this suitability increase, evidence consistent with climate change playing a role in recent DC expansion in phenologically constrained states. We then apply the model to projections of future climate under the RCP45 and RCP85 scenarios and estimate an additional 126–239% increase, respectively, in DC area.