Another option
Last year the wife and I flew into O'Hare and rented a mini van from Enterprise rent a car. It was the absolute most painless way to get to Oshkosh. We flew non-stop to Chicago in about 2 hours. Stepped outside the door from the luggage carousel, got onto the Enterprise rent a car bus that drove us to their facility. We had reserved the mini van weeks before. Took about 15 or 20 minutes to finalize the papers for renting the van for the week and drove directly onto the interstate on ramp right outside the parking lot of Enterprise and headed north to Oshkosh. The route was all interestate through Milwaukee, up to Fond Du Lac and on to Oshkosh. We met our friends who flew into Fond Du Lac and picked them up at the airport. We drove onto Oshkosh and spent the week driving six people around in the well equipped mini van.
It was a perfectly painless trip. Quite enjoyable. If we go again we will go this route. We had looked at flying into Madison, Milwaukee, Appleton, etc. but every flight that flew into those airports required us to fly into O'Hare and catch a connecting flight from there into one of these other places. The wait in between connecting flights was longer than the time it took us to rent the mini van and drive up the interstate to Oshkosh from O'Hare.
If you have not looked into flying into Chicago you should do so. It was a very pleasant experience for us. Oh, by the way, we flew Southwest into Chicago. It was the cheapest fair we found. It did not even require going to any of the discount houses to get the cheapest fair. We just logged onto Southwest's website and plugged in our flight info. Very easy experience for this trip.
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