Due to increasing demand for higher performance, greater flexibility, smaller size, and lighter weight in electronic devices, extensive studies on flexible electronic packages have been carried out. However, there has been little research on flexible packages by wafer level package (WLP) technology using anisotropic conductive films (ACFs) and flex substrates, an innovative packaging technology that requires fewer process steps and lower process temperature, and also provides flexible packages. This study demonstrated and evaluated the reliability of flexible packages that consisted of a flexible Chip-on-Flex (COF) assembly and embedded Chip-in-Flex (CIF) packages by applying a WLP process. The WLP process was successfully performed for the cases of void-free ACF lamination on a 50 μm thin wafer, wafer dicing without ACF delamination, and a flip-chip assembly which showed stable bump contact resistances. The fabricated COF assembly was more flexible than the conventional COF whose chip thickness is about 700 μm. To evaluate the flexibility of the COF assembly, a static bending test was performed under different bending radiuses: 35 mm, 30 mm, 25 mm, and 20 mm. Adopting optimized bonding processes of COF assembly and Flex-on-Flex (FOF) assembly, CIF packages were then successfully fabricated. The reliability of the CIF packages was evaluated via a high temperature/humidity test (85 °C/85% RH) and high temperature storage test (HTST). From the reliability test results, the CIF packages showed excellent 85 °C/85% RH reliability. Furthermore, guideline of ACF material property was suggested by Finite Element Analysis (FEA) for better HTST reliability.