Trips with George Michael

So last week, I talked about my France trip planning. This week, I want to talk about planning a holiday with my pup. GM rarely comes on holiday with us. We usually get someone to dogsit and he sits at home (probably moping) while the rest of us are having fun.

The only vacation I've taken with George Michael, in his 6 years of being alive, was a short weekend ski trip to Vermont. He had a good time with me, taking walks through town and on the hotel property but it wasn't exactly the best experience for either of us. I felt guilty leaving him alone in the hotel room but I also wanted to be out and about. Next year, I'd also like to take a trip that the entire family would enjoy.

Here are my ideas so far:
Luckily, GM is small enough that he would count as carry-on luggage if we need to take a flight. I'm leaning towards Chicago (despite having been there before) because it's lunchtime as I'm writing this and I could really go for a Chicago-style hotdog. Apparently my stomach dictates all of my trip decisions.