[Where to shoot skeet around Chicago?]

If you go to the NSSA website, I think there is a link to skeet ranges in your area.

[Bio vs Pitch target hardness/breakability]

Bio targets are usually a little harder to break than pitch targets. The difference is very small between the two.

[Clays vs 700-x propellant]

I use 700x in my 12 ga skeet loads. It is somewhat clean and functions my 1100 Competition just fine. Never used Clays so I can't really make a valid comparison between the two, but 700x is cleaner than Red Dot.

[Skeet <=> Five Stand?]

No,they are not. They can be shot on the same field but have totally different targets. 5 stand has five stations, Skeet has eight. Skeet has the high house and the low house for targets. 5 stand has five stations with a variety of 8 traps comming from all directions usually shot in pairs except for the first target.

In five stand, each shooter stands in one of the five stations. Usually, there are 2 sets of targets which can be thrown from each station. In our 5 stand, there are 8 traps all in different directions. Each station has a sheet which tells you which targets are going to be thrown and what order they should be shot at. You usually need more than 25 shells for a round of 5 stand because you can shoot more than 1 shot at the first single target if you miss with the first shot. There are 5 targets per station. 1 single and 2 pairs.

Skeet is a very different game. The targets are always shot from the high house or the low house and pairs. Each shooter starts at station 1 and when the squad is finished they go to station 2, all the way around to station 8. Shooting stations 1,2,6,and 7, you shoot 1 high, 1 low, and 1 pair. At stations 3,4,and 5, you shoot singles from the high and low house. Station 8 is in between the houses and you shoot 1 high and if you don't miss, 2 low houses. In skeet, after your first miss, you shoot an option which is the same target you just missed. If you don't miss, you shoot 2 low 8's for 25 straight.