Retail inequality reduces the convenience of shopping and limits employment in disadvantaged neighborhoods. The successful design of policy interventions depend on whether inequality comes about because retail establishments fail to enter disadvantaged neighborhoods or because establishments fail more upon entering neighborhoods. Our paper addresses this question by predicting establishment entries and exits in the Chicago metropolitan area from 1990 to 2009 through a combination of event-count models of entries and discrete time event history models of exits. We find urban design characteristics, population density and percent homeownership, predict retail entries. The influence of race and poverty on establishment entries varies by industry, though nearly all are less likely to enter neighborhoods with higher proportions of Latinos. In contrast, we find little association between neighborhood race, class, or ethnicity on the likelihood of an establishment exiting the neighborhood. Our results suggest that lower rates of entry, rather than different rates of exit, create retail inequality by race, class, and ethnicity in the Chicago metropolitan area. Policy makers can use this information to tailor policy solutions that address retail inequality.