Polychlorinated Biphenyls (PCBs) are persistent organic pollutants known for their toxicological effects. Though industrial production of legacy PCBs was banned in 1977, they can still be measured in nearly all environmental matrices. The Chicago Sanitary and Ship Canal (CSSC) is lined with industry and the receiving waters to the Stickney Water Reclamation Plant, the World's largest waste water treatment plant and was therefore speculated to be a potential source of PCBs to the Greater Chicago Area. Surficial sediment samples were acquired along a 45 km stretch of the CSSC, from Kedzie Ave. to Lockport. PCBs in the bulk sediment were extracted using accelerated solvent extraction while PCBs in the porewater were extracted using solid phase micro extraction. The PCBs were identified and quantified using a variation on EPA method 1668C. A total of 176 individual and coeluting PCBs were identified and quantified in this study. The sum of PCB concentrations in the bulk sediment was found to range from 70 to 4970 ng/g dry wt. The sum of PCB concentrations in the freely dissolved sediment-porewater was found to range from 2 to 366 ng/L. The bulk and porewater concentrations were used to estimate an average mass flow rate of PCBs through the CSSC of 368 kg/y. The large mass flow rate of PCBs passing through the CSSC and the fact that the CSSC connects Lake Michigan to the Mississippi River suggest that continued monitoring of PCB concentrations are necessary to better understand the transport and fate of PCBs in and out of the Great Chicago Area.