I do. 4 flat miles looping around, then 3 miles or so up 800 ft. Then 3-4 more rolling on top of a ridge. Run to the start to warm up. Jog down for a cooldown.
Also have a 5.75 mile climb of rolling/step-wise climbing, 1050', then a rolling loop around the top of the hill.
I use them often. Once a week when I am building a base. They are my first workouts before anything else. I run them hard, sometimes really attacking, because the hardest I can do them uphill isn't enough to wear me out long term. (As opposed to overcooking a flat 10 mile and being too banged up to hot the rest of the week well.) Quads are sore at first, but I start at 25 minutes. Then 35', 45' 55', and then at 65' I start trying to hit the last 20' or so, the top-of-hill miles. faster than the week before.
Some maintainane during the next phase. Depends on the goal though, if I'm training for a marathon or 5k. Sometimes I run these maintainance workouts moderately, 20" slower than before, saving the legs for the faster stuff but still touching that base just enough to maintain it for the next 16 weeks.
As for you, I have gone to Waterfall Glen to park, then warmed up out 91st to the bottom of the hills at Wolf. Head North and left on german Church road to start climbing. Left on Madison if you want to loop again, just try to finish on top of the hills. Same thing out by Palos. Park, warm up to the Canal somewhere. Start on a road next to the Canal, then wind your way up.
Not too steep. Not more than 4% average for several miles for example. I would avoid any 10%+ ramps for more than 100m in the middle too. Too steep to run fast. 7% for 600m? Suck it up and make that yours. 7% for 2k? Probably too much.
Just my perspective.