Accurately predicting the overlying pressure is crucial for determining an appropriate cover depth of underwater box tunnels to avoid the uplifting failure. Based on the project of box jacking crossing the Beijing-Hangzhou Grand Canal in Suzhou, the characteristics of overlying pressure variation during tunneling are investigated. The monitoring results reveal that the fluctuation of overlying pressure is weakened during the rapid tunneling process. A modified analytical model for vertical earth pressure is conceived, in which the active and passive limit states for multi-layered soils are both considered. The probable range of overlying pressure obtained by the proposed model is suitable to cover the actual values. The anti-floating behavior of underwater box tunnels for two different working conditions is discussed by calculating the minimum cover depth. Using the calibrated analytical models, a parametric study is conducted to explore the influence of injection pressure, hardened slurry unit weight, soil internal friction angle, soil cohesion, and tunnel geometry. It is found that the injection pressure during the construction process is crucial for determining the necessary cover depth, and the change of box tunnel height makes it easier to trigger the variation of minimum cover depth.