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Why isn't your SO flying in with you in the mass arrival or riding with your mom? And will your kid ride along to pick her up? Seems like way too much trouble for someone who doesn't want to be there. Is she all that enthusiastic about visiting your extended family in Chicago? I say tell her it's just not feasible to pick her up, but you'd love for her to fly in with you next year.
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Airline to Milwaukee is likely to be cheaper. But if there is a aviation convention in Milwaukee I haven't heard about it. You are 90 miles away from Osh, so almost a 4 hour round trip drive probably in a lot of traffic. But of course its your choice to do it that way. I stayed in Milwaukee one year at a friends place for free just across the street from Mil airport. I didn't like driving.
I have had family and friends fly into App, and it was so easy there on the airline.
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I don't think many can find a direct airline flight to Appleton. It usually takes an extra connection to Appleton (sometimes 4 hour wait) and many more hours to actually get to Airventure.
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There are direct flights to ATW but they aren’t many. All depends what hub you fly out of. Delta does a couple a day from ATL.
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Whether or not there are direct flights INTO Appleton, Milwaukee, or Madison is a kind of a moot point. We live in Albany, NY, and about the only places you can fly OUT of here direct to are Chicago, Detroit, and Baltimore. There are a few flights from here to Appleton that have only 1 connection, but the fares are about $100 higher. There are many more options flying into the others from here.
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That's why flying direct to Mikwaukee is the cheapest, fastest and best option for me from Seattle, and maybe most of the country.
It's too bad EAA doesn't help much (or any) promote transportation from Mikwaukee for us non-Wisconsin members.
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I’ve got extended family in the area and there’s really no convenient shuttle service from Appleton, Neenah, Menasha, Oshkosh or Fond du Lac down to MKE. There is a bus but it takes hours due to its multiple stops. Most just drive down to MKE. Guess the demand just isn’t there.
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That lack of transportation between Oshkosh and Milwaukee is why EAA should look at some options for the Airventure week.
I wasted untold hours researching and finding a new bus service in 2019. I booked a ticket for the one daily bus but the airline was late and I missed it. Fortunately, another EAA pilot I had met on the airline gave me a ride.
But I won't risk getting stuck at MKE again with no way out. So it looks now like my best future option is going back to driving to Airventure like I always did.
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I have had friends use the bus from Milwaukee to Fon du Lac, don't recall it making any stops along the way. I m not sure if it goes on to Osh or not, they have used it both ways.
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I usually come and go several times during the Oshkosh show, whether we're running up to Brennand or some other place for a shower, picking someone up at another field, flying out to Shawano, or just giving rides to the volunteers. It's never a problem. Handy to have a sign with your row number to get back, but its never been a problem.