Pour water, 1/2 cup sugar, salt, and vegetable oil into a medium sauce pot and whisk together. Bring contents to a boil and remove pot from heat.
Add in flour and mix until dough ball forms.
Use a pipet and bag or large freezer bag. (Use scissors to cut lower corner of bag to make pipet. Cut about 1/4 inch away from corner.) Place dough in bag and push to the corner with the hole.
Heat medium sauce pot with vegetable oil to 360℉.
Over oil, squeeze dough roughly 2 inches and cut with scissors to drop into oil. Fry until golden brown. Remove from oil and place in paper-towel lined bowl to drain. Add cinnamon, rest of sugar, and toss churros in mix.
In another pot, combine heavy whipping cream, butter, and chocolate chips over medium heat. Continuously stir to allow chocolate and butter to melt and spread. Once smooth chocolate sauce is formed remove from heat.
Dip churros in chocolate sauce and enjoy!