I planned a trip from Atlanta up to oshkosh one year. It boils down to the same thing, either you've got to hug the shoreline of lake michigan or go way around to the west. Why don't you do this. Plan two trips. (You'll have fun) The ORD class B is 10000 ft, Plan a trip at either 11500 or 12500 as the case may be. If the weather is CAVU, fly the high altitudes. If on the other hand, the ceilings are say 5000 ft., plan a shore hugging route or a way out west route. Load them both in your GPS, and when the day comes, you're set for clear and a million or down low. ( If you "do" go above ORD's Class B, call approach anyway and just tell them what you're doing. They liked it when I did this.)
There "are" a lot of very good intersections along the lake shore you can use and I highly recommend them. The down side is try to find them on a sectional or AOPA's flight planner sectional. I personally use Garmin Pilot, and they are very very easy to see and will make life much easier for you vs making a dozen personal waypoints. (Disclaimer-- I've got no personal interest in Garmin Pilot---I'm sure foreflight or other programs are just as good.)
I just looked on my Garmin 496. They show there too, BUT I had to go all the way down to the 3 mile scale before they would show. Just northwest of Gary IN, and east of Midway, there's orrin, niles, bebe, cabij for starters. You'll see. Just watch the bottom of the ORD Class B altitude restrictions, line up these shore hugging waypoints, and you'll be fine. Almost forgot--watch your Midway Class C altitude restrictions also, but easy to see on your GPS.
