A system and method for allowing a user to schedule pickup of an ordered item provides a user interface having user interface elements for allowing a user to specify a frequency with which an order is it to be picked up, for informing a user as to availability of the item for pickup, and/or for allowing a user to request that an item be held in reserve for pickup within a given period of time, such as 24 hours. Frequency options provided to the user for selection when scheduling an order for pickup may include a one-time frequency, a daily frequency, a weekly frequency, a monthly frequency, and user specified dates. The information as to availability of the item for pickup is determined considering a time of order and real-time stocking information for the item.