Yes, there has been a notable example of an airplane reaching the edge of space: the North American X-15. The X-15 was a rocket-powered aircraft that conducted a series of test flights during the 1960s. Some of its missions reached altitudes over 100 kilometers (approximately 62 miles), which is commonly recognized as the boundary of space according to the Fédération Aéronautique Internationale (FAI).
Additionally, spaceplanes like the Space Shuttle have also operated in the realm of atmospheric flight before transitioning into space. However, the shuttle's design was fundamentally different, as it was primarily intended for space missions rather than standard atmospheric flight.
More recently, commercial ventures such as Virgin Galactic and Blue Origin have developed suborbital spaceplanes (like VSS Unity and New Shepard) that aim to take passengers briefly into space, marking a new era of space tourism. These craft operate similarly to airplanes but are designed to reach the edge of space.