First off, I think you need to define "Friendly". When it comes to controllers, you will find them curt, colloquial, stressed, rushed, angry, and sometimes humorous. I think of the Chicago airspace as a compressed version of So Cal (San Diego to Van Nuys). O'Hare alone fluctuates (between one and two) as the busiest airport in the US, and in terms of traffic, the Chicago airspace is among the top three busiest in the world (New York, London, and Chicago). Thus, VFR is discouraged almost by default alone.
Now, as you know, and I don't have my Chicago sectional out...ORD is class B. You, as PIC, need to have your PPL at the very least if you wish to land or take off there. NO EXCEPTIONS. You also must have a two way radio and a mode c to get into the Chicago airspace (since it is just about all C veiled where you want to go)--which you have in the Warrior.
Before we get into options for you, I have flown into Meiggs, Palwaukee, O'Hare, Midway, and Glenview NAS (when it was open). Palwaukee presents a unique challenge because every King Aire and Lear in the Midwest seems to be there on severe clear afternoon days competing with the Dentists and Lawyers out building time. I have seen an airplane (believe it was a Cherokee 6 cut off a 172) in the pattern. I have seen fist fights break out on the ramp. The controllers have broken FCC rules using colorful language there. If you choose Pal-Waukee, keep your head and a$$ wired tight. To this day, I never see aircraft anywhere else taxi like they do at Palwaukee--FAST. I went in and out of MDW in 1986 when I was getting my PPL. Back then it was busy--nothing like Palwaukee--but the only airline traffic was a few 737s from Midway Airlines, a few Midstate Metros, and a very occasional UA or NW 727.Southwest then, was considered a fad.. MDW was an airline ghost town, but busy GA-wise. Today is a different story. MDW is C. You can get servicing through Million Aire or Signature, but you must follow C rules--yeah, GA VFR is possible, but not "friendly".
So, forgive me if I'm belittling you, but this is for our general av buffs...
(1) To get into Midway you need to squawk C and have a two way radio.
(2). So, you must be talking with the appropriate ATC facility and contact with postion, altitude, becacon code, destination, and request class C service--memorize the sectional and choose a way-point (which would be marked with a flag) outside the C ring to report in.
(3). Even if the controller responds with YOUR CALLSIGN (n-number) and "stand bye" go ahead and enter the airspace since the requirements for two-way have been met.
(4). If the controller (pay attention here) responds without saying your call sign, the REQUIREMENTS ARE NOT MET. YOU CANNOT ENTER THE AIRSPACE.
(5). You must establish ATC procedures ASAP when departing class C.
(6). In general, VFR aircraft will maintain visual sep in C. 2500 feet vertical.
(7). You will be sequenced
(8). You get RADAR service according to whether or not the controllers are busy (which they will be).
WRT Meiggs. It is right on the outer ring of C (imagine that) so you need to fly VFR approach corridor from the south (which is published on an approach plate) or at least you used to. Very busy and scrunched under both ORD and MDW. Has had a mid-air or two to emphasize the importance of being alert.
If you want a less challenging stop over on a long x-country, I would suggest going up north to MWC. Timmerman in Milwaukee. Got a great restaurant on the flight line called the Sky Room. They are real GA friendly.
But, if you like to live on the edge...MDW is varsity for VFR. PalWaukee is like a New York Cab Stand, and Meiggs can be interesting. Good luck, and review your sectional thoroughly.