Increased plantar fascia thickness is common with chronic plantar fasciitis, and reduction of the thickness after extracorporeal shock wave therapy or steroid injection has been reported. We hypothesized a decrease of plantar fascia thickness was associated with pain reduction after extracorporeal shock wave therapy. Fifty-three eligible patients with 78 symptomatic feet were randomly treated with piezoelectric-type extracorporeal shock wave therapy of two intensity levels (0.12 and 0.56 mJ/mm2). Two thousand shock waves for three consecutive sessions were applied at weekly intervals. A visual analog scale for pain, the Foot Function Index, the Short Form-36 Health Survey, and ultrasonographic measurement of plantar fascia thickness were evaluated at baseline and 3 and 6 months after treatment. We analyzed the association between pain level and plantar fascia thickness with generalized estimating equation analysis and adjusted for demographic and treatment-related variables. Patients with thinner plantar fascia experienced less pain after treatment; high-intensity treatment and regular exercise were associated with lower pain level. The overall success rates were 63% and 60% at the 3- and 6-month followups. High- and low-intensity treatments were associated with similar improvements in pain and function. Receiving high-intensity treatment, although associated with less pain at followup, did not provide a higher success rate.