In the re-emergence of Highly Pathogenic Avian Influenza (HPAI), live bird markets have been identified to play a critical role. In this repeated cross-sectional study, we combined surveillance data collected monthly on Jakarta's live bird markets over a five-year period, with risk factors related to the structure and management of live bird markets, the trading and slaughtering of birds at these markets, and environmental and demographic conditions in the areas where the markets were located. Over the study period 36.7% (95% CI: 35.1, 38.3) of samples (N = 1315) tested HPAI H5 virus positive. Using General Estimation Equation approaches to account for repeated observations over time, we explored the association between HPAI H5 virus prevalence and potential risk factors. Markets where only live birds and carcasses were sold, but no slaughtering was conducted at or at the vicinity of the markets, had a significantly reduced chance of being positive for H5 virus (OR = 0.2, 95% CI 0.1-0.5). Also, markets, that used display tables for poultry carcasses made from wood, had reduced odds of being H5 virus positive (OR = 0.7, 95% CI 0.5-1.0), while having at least one duck sample included in the pool of samples collected at the market increased the chance of being H5 virus positive (OR = 5.7, 95% CI 3.6-9.2). Markets where parent stock was traded, were more at risk of being H5 virus positive compared to markets where broilers were traded. Finally, the human population density in the district, the average distance between markets and origins of poultry sold at markets and the total rainfall per month were all positively associated with higher H5 virus prevalence. In summary, our results highlight that a combination of factors related to trading and marketing processes and environmental pressures need to be considered to reduce H5 virus infection risk for customers at urban live bird markets. In particular, the relocation of slaughter areas to well-managed separate locations should be considered.