Beat 4oz cream cheese with 2 1/2 tablespoons sugar & 1 tsp vanilla until smooth.
Press the rolls together & roll them into a large rectangle with a rolling pin. (using a silicone baking mat. Spread the cream cheese mixture in the center 1/3 of the rectangle. Top the cream cheese with the cherry pie filling, & then top the cherries with the chocolate chips.
Using a pizza cutter, cut 1" tabs on both sides of the filling, as close as you can get to the filling without making a mess of your pizza cutter. Then grab a tab from one side, pull it out to the side to stretch it, then lift it up & over the filling all the way across. You want your tabs to go as far as they can across the center so they don't come un-tucked. Repeat with the rest of the tabs, alternating sides in a criss-cross motion to create a braid. Pinch & tuck the ends the best you can so the filling won't squeeze out.
Let rest 10-20 minutes.
Bake at 350˚F for 30-40 minutes or until the dough between the braids is done. Cover with foil the last 15 minutes.