Paleosols occur in the Driftless Area of southwestern Wisconsin because this area escaped direct Pleistocene glaciation, allowing long-term loess and colluvium accumulation in selected settings. The most complete known depositional sequence at Oil City, Wisconsin, contains eight lithologic units with five paleosols, all with normal remanent magnetism (i.e., <780 ka). Previous work characterized the stratigraphy, pedology, micromorphology, and clay mineralogy of the section. We investigate chemical weathering of the 8–63 µm silt fraction using X-ray diffraction (XRD) and elemental geochemistry by portable X-ray fluorescence (pXRF). Elemental ratios TiO2/CaO, Zr/Sr, and Rb/Sr generally align with the pedological evidence of weathering. Mineral ratios plagioclase/quartz and K-feldspar/quartz display greater scatter and less certainty in interpretation. The paleosols with Bt horizons have ratios indicating greater weathering than the modern soil. The most weathered paleosol is formed in the unnamed fourth loess unit stratigraphically below the Loveland Member. The stratigraphic position and higher degree of weathering support correlation of the fourth loess with the Yarmouth Geosol and Crowley’s Ridge Silt of the Middle Mississippi valley. Geochemical indices by pXRF are more consistent with established lithologic breaks than mineralogy by XRD. Our results support the use of pXRF for stratigraphic and weathering studies of Quaternary sediments.