I don't know Chicago, other than it seems like a huge portion of elite skaters train there, so you folks must be doing something right.
I do have four minor suggestions:
1. Take more USFSA LTS or ISI WeSkate classes. They provide fairly cheap, fairly focused ice practice time, under a degree of supervision. At most rinks I know, lessons are on evenings or weekends, and there is usually a public session just before and/or just after the set of classes. BTW, one thing classes don't provide (unless you take power skating classes) is endurance training. Off-ice training can supplement.
2. Cross country skiing is great off-ice training too - many muscles in common.
3. I don't know about you, but for me, a lot of skating issues relate to muscle strength and flexibility. I need muscles to do deep knee bends, on one and two feet. I need muscles to push my limited flexibility. I need muscles to push and pull against edges. There are a lot of exercises you can do at home that build the same muscles, and that stretch my flexibility. But maybe those issues don't apply to you.
4. Run or jog during off-work hours. Probably the best possible overall conditioning exercise you can do, and strengthens your legs and core besides. Learn to keep your feet low to the ground so you glide through and don't have hard impacts - race walking technique works fairly well, or you will be hard on your knees. If it's a little cold, wear a scarf, so your breath isn't cold enough to freeze your lungs. If it's a lot cold - forget it, unless you have a gym with an indoor track.