This Airband Transceiver can be used not only to monitor the air bands and the weather stations, it is also an important tool that should be in your flight bag, whether you are flying a manned aircraft or as a Part 107 Remote Pilot.
Chromebook? I am not sure. You will have to contact Yaesu regarding this. Headset? Yes, there is an adapter plulg that goes into the radio and adapts to 1/4 in. avionic headsets.