From the UK - I have done it on an organised trip a couple of times but found it much easier to do it myself these days. Last year I flew to Detroit then to Green Bay the weekend before the show, visited friends in Door County for a few days before driving to Appleton to stay. Fairly easy drive down I41 to Oshkosh and back each day. Flewback from Appleton via MSP and Detroit
One other thing to consider is the cost of a rental car, if you go that route. I don't know what the "off the street rate" is, but for me (I am able to receive a heckuva deal thru corporate discounts), same number of days out of MKE is at least $200 less than ORD, simply going on the fees and taxes and surcharges they charge. MKE is also about an hour closer to OSH, but if you're making connecting flights that point may be moot. I don't understand why some folks above noted that MKE is a harder drive; if you take the feeder out of the airport, it dumps you right on the same interstate (94/41) that you'll be on anyway out of Chicago.
Just thought of another factor: your return date. We made the mistake of booking an evening flight out of ORD one year. All was great driving back to ORD until we got about 30 miles from ORD. We were stopped dead for no other reason than Friday afternoon rush hour. It took over an hour to go that final short stretch of road. Oh, and bring exact change for the toll booth, or pay another $5/day (just guessing) to activate the toll reader in your car in addition to the tolls themselves.
This will be my third visit (from NYC). I fly into Chicago and rent a car. I stay in the dorms and use the bus pass. This gives me a lot of flexibility. I can hop out to the store for supplies, I can set my own schedule and attend events that are off the field. If I had enough time, I would drive my truck and would consider camping, but it woud double my travel time.
Of course, when I finish my airplane, I plan to fly in, but that is a few years off at this point.
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