Start searching for your trip by looking at skyscanner. This app/website is free to use and hellps you find the best flights from your airport! This is one of my favorite travel hacks!
Once you know the destination you'd like to visit, use the app hopper and google flights to determine the best time to book your flights.
CHeck booking sites like Booking dot com, hotels dot com and vrbo - they all have pretty good free cancellation policies.
Next, use pinterest and blogs to find the best things to do in your destination. Mark the locations as favorites on your google maps!
sign up for all programs to collect points (hotels/airlines) and have the right credit cards in your pocket so you can use your miles to travel free!