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More expensive helmets tend to have better retention systems that hold the helmet more securely while also being more comfortable.
More expensive helmets tend to have better ventilation, which can make the helmet more comfortable in the heat.
More expensive helmets tend to be lighter, which can make the helmet more comfortable on long days.
More expensive helmets tend to have a better aerodynamic profile, which can make you faster.
None of these things are absolute rules, and the most important thing is that the helmet fits you well. I personally have been very happy with helmets with an MSRP in the $150-200 range, often found on sale for $75-125. I prefer these to the truly "cheap" helmets, but there are surely diminishing returns the more money you spend (which is not to say that someone with the money could not find a $300 helmet worth it).
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