If the earth was really spinning in one direction at 1,040 Miles Per Hour the planes in my earlier scenario could not reach their destination at about the same time.
Sure they would. Let's say a plane is traveling from the west toward the east, the same direction the earth rotates. The plane is already traveling at a speed of 1040 MPH while it's still on the ground, but so is the earth. So in order for the plane to make any progress towards the east it has to be traveling more than 1040 MPH. So let's say the plane flies at 500 MPH. At this speed 1040 + 500 = 1540 MPH, the plane will will out-pace the earths rotation by 2000 miles in 4 hours. In other words a plane flying at 500 MPH will complete a 2000 mile trip in 4 hours.
Now consider the trip in reverse.... east to west. Again, the plane is traveling at 1,040 MPH before it even leaves the ground, so in order for that plane to make any progress towards the west it has to be traveling at less than 1040 MPH. So again let's say the plane flies at 500 MPH. At this speed 1040 - 500 = 540 MPH, the plane lags the earths rotation by 2000 miles in 4 hours.
Think of it like an ant on a spinning basketball... the ant travels across the ball at the same rate of speed releative to the ball no matter what direction the ant travels or the ball rotates.