Quantum Entanglement is the essence of quantum physics and inspires fundamental questions about the principles of nature. Moreover it is also the basis for emerging technologies of quantum information processing such as quantum cryptography, quantum teleportation and quantum computation. Bell's discovery, that correlations measured on entangled quantum systems are at variance with a local realistic picture led to a flurry of experiments confirming the quantum predictions. However, it is still experimentally undecided whether quantum entanglement can survive global distances, as predicted by quantum theory. Here we report the violation of the Clauser-Horne-Shimony-Holt (CHSH) inequality measured by two observers separated by 144 km between the Canary Islands of La Palma and Tenerife via an optical free-space link using the Optical Ground Station (OGS) of the European Space Agency (ESA). Furthermore we used the entangled pairs to generate a quantum cryptographic key under experimental conditions and constraints characteristic for a Space-to-ground experiment. The distance in our experiment exceeds all previous free-space experiments by more than one order of magnitude and exploits the limit for ground-based free-space communication; significantly longer distances can only be reached using air- or space-based platforms. The range achieved thereby demonstrates the feasibility of quantum communication in space, involving satellites or the International Space Station (ISS).