Aircraft and control tower radios are low powered. Therefore, depending on terrain, range will be limited. This is not a problem because aircraft communications tend to be line of sight. However, ground control and tower frequencies can be difficult to hear at 10 miles. Have you tried approach and departure frequencies? These tend to be much easier to hear. Check airnav.com for the frequencies in your area.
Vertical dipole questions come up in these threads frequently. They seem very simple to build, but can be problematical. For aircraft reception they are not very broadband for a spectrum that is 18MHz wide. Any dipole is a balanced load. That is, feeding it directly with coax is going to be less than optimal. A 1:1 balun is needed. Some use ferrite chokes or coils of coax at the feed point. These are not recommended. The feed line should run at right angles to the antenna for a quarter wavelength to avoid interaction with the antenna. The antenna should be mounted free of obstructions.
Having said all that: A discone is a better choice for monitoring air frequencies. It is broadband and can be fed directly with coax. It will also cover military aircraft frequencies. No they do not have any gain. However, the flat frequency response is more important. Remember that you are mostly hearing line of sight transmissions anyway.