Costs of production and organic price premiums are defining factors influencing the economic viability of organic crop production systems. Different agronomic practices, such as crop rotation and tillage intensity, are known to affect the economic performance of the production systems. The aim of this study was to compare the impact of two crop rotation sequences (simplified and diversified) and two levels of tillage intensity (high and low) on the cost of production, gross return and gross margin of crops when grown under organic management in the semi-arid Brown soil zone of the Canadian Prairies. The 2-year simplified rotation sequence consisted of forage pea (Pisum sativum L.) grown as a green manure followed by hard red spring wheat (HRSW) (Triticum aestivum L.), while the 4-year diversified rotation sequence was forage pea green manure followed by flax (Linum usitatissimum L.) or yellow mustard (Sinapis alba L.), field pea or lentil (Lens culinaris L.) and HRSW. Our hypothesis that a more diversified crop rotation would increase profitability over a traditional simplified crop rotation was supported by the findings. However, the findings did not support our hypothesis that reducing tillage intensity, and the combination of tillage reduction and diversified crop rotation through a synergetic response, would further enhance profitability. Analysis of the breakeven prices and breakeven yields for crops indicated the importance of adopting diversified crop rotations and choosing crops with high organic price premiums as means to maximize the long-term profitability of organic cropping systems.