Sorry I can't be of more help, but being from the midwest and camping a lot (have you looked at Nordhouse Wilderness area on the Michigan side? Googlemaps gives it 5hrs--I'll post the gmaps link at the bottom. Though it could be 6 hrs depending on where in Chicago you're coming from.
As far as bugs, nada. Weather? I've camped out at Nordhouse in late october and it was early-winter conditions, cold, blustery, no people, frosty, most of the leaves off the trees. but very pretty! and we think a cougar or something followed our tracks at night when we came off a big dune and went to the lake and back. I've also been there in early-mid october and had total indian summer, incredibly leaves, pleasant at the beach. Even in summer the lake breezes can sometimes be beneficial enough to keep any bugs at bay.
It is a decent first backpacking trip, perhaps with 20 miles total of trail available, you can go as long or short as you like. Some of the big dunes right on the beach that are well wooded at their top have some primo camp spots.