Winging something is when you are not prepared but decide to do it anyways to see what happens. Off the cuff is similar... doing something spontaneously. Playing it by ear is when there is no set plan of action and you’re going to adapt to the scenario as it unfolds. They are all rather similar but more appropriate in some contexts... I would say winging something has an element of danger whilst playing it by ear can be a logical option. Hope this helps :)

Thank you Rohan, now their meaning is clearer.