Job Search Timeline

I've been applying to a handful of jobs over the past few months. As most of you know, it becomes a full-time job after a while, but I'm making more of an effort to put the time into the search. I feel like I've luckily been able to get contacted somewhat quickly in the past, but it seems like this time around has been dragging on. Do you try to reach out to the hiring manager or someone at the organization? Should I be more patient in hearing back? I also feel like heading into the holiday season becomes even tougher to connect with people. Any and all tips welcomed!