An on-demand insurance (ODI) server for generating dynamic user offerings may be provided. The ODI server may include at least one processor in communication with a memory device. The at least one processor may be programmed to (i) receive, from a user computing device associated with a user, an insurance policy request for a trip from a start location to an end location, (ii) determine at least one transportation mode available for the trip, (iii) access contextual data associated with the trip, (iv) assess a risk associated with the at least one transportation mode, (v) calculate a risk score associated with the at least one transportation mode based upon at least the contextual data, (vi) generate an insurance offering associated with the at least one transportation mode, and/or (vii) transmit the insurance offering in real time to the user computing device for purchase by the user.