The use of 2,5-dimethylfuran (DMF) and acrylic acid (AA) as the reactants to produce aromatics catalyzed by Bronsted acid ionic liquids (ILs) has been achieved successfully under mild conditions. The whole conversion process including Diels Alder (D-A) cycloaddition, ring-opening/decarboxylation, and dehydration was investigated by density functional theory (DFT) calculations which were also verified by experiments. Two pathways for the activation of DMF were proposed: unprotonated oxygen of the DMF (UPOD) and direct protonated oxygen of the DMF (POD). In the UPOD pathways, two routes (endo and exo), in which the overall rate was limited by the ring-opening step, produce p-xylene or 2,5-dimethylbenzoic acid (DMBA), respectively, whereas in POD pathways, the limiting step of DMBA production was attributed to the D-A cycloaddition. The role of Bronsted acid ILs was mainly reflected in the proton transferability. The present study provides basic aids to understand the mechanism of converting furanics and AA into aromatics catalyzed by Bronsted acid ILs.