I’m writing this in pieces so bear with me.
To/from ORD, I think 06C is a touch closer by car than PWK. Also I would expect PWK to be $$$$$$$$ (use Hawthorne) compared to 06C’s $$$$. At 06C you have a plethora of tie down spots and even an option to put it in a hangar. The only real disadvantage to 06C is sometimes you get a stiff crosswind (runway is 11/29 with buildings north and trees south). Though at PWK they’ll land you on 16, even with a decent tailwind… not my favorite.
Chicago Approach does not provide instrument services to 06C. They’ll get you close but you have to cancel. It sits under a 1900’ Bravo shelf and has no approaches.
If it were me, it would be based on weather. Anything better than garbage weather I would opt for 06C. If it’s really nice weather, fly up the Chicago lake shore, then are the “Eisenhower transition” at 1600-1700 MSL under the Charlie and Bravo. It follows I-290 and is a neat short cut. Emergency outs are typically parks and parking lots. If the weather isn’t spectacular, I’d swing around south of KMDW and stay in as high of a bravo shelf as you can (like the 3000’ shelf). You’ll get loads of thermals in the summer. On a hot day (like middle of next week), you can expect moderate turbulence, especially over the warehouse district.
If it’s IFR and you’re coming from the south, I’d also take a close look at DPA or GYY. They have lots of good instrument approaches and are on “the south side” of the airspace. I don’t know how bad the vectors are to get into PWK from the south under IFR. Let’s just say you may save time landing at DPA (further out) than getting vectored half way across the state.
With respect to comms, Chicago approach is great. I try to be on FF as much as I can. I’d say lake shore and Eisenhower transition, definitely do FF. Helicopter tfc gets naughty and not a lot of space to maneuver sometimes.
Edit: Eisenhower transition takes you westbound from Lake Shore/~Sears Tower towards KDPA
