This paper investigates food price dynamics and inflation inequality in Italy by leveraging web-scraped data from major retailers. In the aftermath of the COVID-19 pandemic, surging food prices have disproportionately affected lower-income households, which allocate a greater share of their expenditure to essential goods. Drawing on over 5 million high-frequency price observations from 2021 to 2023, we examine within-category price variations across regions and time for staple food items, with a focus on Milk and Olive Oil. Using a modified version of the Time-Interaction-Region Product Dummy (TiRPD) model, we construct sub-national price indices across different price deciles, enabling a detailed assessment of inflation heterogeneity. Our results reveal that the lowest-cost items within each category experienced faster price growth compared to higher-priced counterparts—a dynamic known as “cheapflation”—thus limiting the ability of consumers to mitigate inflation by substituting down in quality. These patterns are consistent across product categories and regions. The findings underscore the need for timely and targeted policy interventions to mitigate the regressive effects of inflation and to protect vulnerable households.