Although a wide range of literature has investigated the network-level highway maintenance plans and policies, few of them focused on the maintenance scheduling problem. This study proposes a methodology framework to model and compare two different maintenance scheduling strategies for highway networks, i.e., minimal makespan strategy (MMS) and minimal increased travel delay strategy (MITDS). We formulate MMS as a mixed integer linear programming model subject to the constraints of the quantity of manpower and the worst-first maintenance sequence. A bi-level programming model is proposed to quantify and optimize MITDS. The upper level model determines the optimal scheduling to minimize the increased traffic delays during the maintenance makespan. In the lower level, a modified day-to-day traffic assignment model is put forward to reflect the traffic evolution dynamics by simulating travelers’ route choice behaviors. A simulated annealing algorithm and augmented Lagrange algorithm are employed to solve the two proposed models, respectively. Finally, a numerical example using a highway network is developed. The two proposed strategies are tested considering different traffic demands, numbers of engineering teams, and travelers’ sensitivities to traffic congestion. The experiment results reveal that compared with MMS, MITDS extends makespan by 2 days though, it reduces the total increased travel delays by 4% and both MMS and MITDS can obtain the minimum total increased travel delays when the number of engineering teams is 6. The sensitivity analysis indicates that both the two strategies have the maximum and minimum total increased travel delays when the weight of prediction in travelers’ perception is 0.3 and 0.7, respectively. The proposed framework has the potential to provide reference in implementing highway maintenance activities reasonably.