In advance: Make cookies. Prepare and roll out dough. Use patterns to cut propeller, wing, tail sections and clouds. Bake and cool.
Bake and cool 1-layer cake. Ice area for windows smooth. Let set then use patterns to mark window edges.
Cover plane, wing and tail section cookies with tip 18 stars. Add tip 5 dots. Position wing and lower tail section at a 30° angle, supporting each cookie with 2 Lollipop Sticks, cut to fit. Insert 2 Lollipop Sticks into cake side at an angle where upper tail section will sit, leaving 2 in. extended. Attach cookie to stick using icing.
Ice propeller and cloud cookies smooth; let set. Cut 2 Lollipop Sticks to 3 in. long; insert into cake side where propeller will sit, leaving 1 in. extended. Attach propeller using icing. Pipe tip 5 outlines at edge and 1/4 in. inside edge; attach spice drop to center.
Pipe tip 4 outline on clouds; immediately sprinkle with colored sugar, shaking off excess. Pipe tip 4 message, tip 5 name.
*Combine Leaf Green with Lemon Yellow for green shown. Combine Violet with Rose for violet shown.