One course that I may be a bit biased(used to be Assistant Super) on that I don't see anywhere here is Ivanhoe. Especially the original 18, why they added the other 9 is mind boggling, or why they didn't keep the original 18 with the extra 9 on the side. But I've been fortunate to play a lot of these golf courses you've all mentioned and I've always thought Ivanhoe offered a very neat experience especially with the diversity in course style with forest, and prairie combined together. Hills did a good job with bunker renovations along with adding some very interesting features around greens complexes. I've always thought that if it was the original 18 and there were no houses on it, it could contend for a top 100 spot.
Jason, Scott at OC has done some awesome work there with bunkers around the greens. Love the par 3 5th now being out there in the wide open, then the bunker work short right of 6 green. Played Old Elm a few weeks back and what Drew did with the bunker renovation along with Curtis's aggressive nature of tree removal has brought that course a mystique and look like no other in Chicago. If anyone wants to see a course taken from over tree'd in the 80's to how it should be put OE on the list. Expansive views and vistas can now be spotted completely around the course and can basically see the whole property from the 8th green.
Great to see my current course Briarwood on some of the lists. The more time I spend here and the more work we do I feel it has some great golf holes. Middle part of the back 9 is phenomenal! So much great golf here in Chicago and I know my peers and I are working our hardest to make it even better and making this area a go to when it comes to playing great golf courses with great conditions.