I was involved with a group where we had regular yearly meetups. Last time I attended was in Seattle, but it's just a group of users from a forum and we all met up for a weekend of drinks, dinner and sight seeing. 50+ people sowed from all over the world - US, Canada, UK, Thailand, Mexico - it was a blast.
Setup a golfing vacation to North Carolina (when there's no tornado or hurricane) and I'm there

I wish the conferences woudl go back to Vegas as flights, hotels, food etc are a lot cheaper for everyone. While Chicago is nice, it can be limiting. At least Vegas I can make a weekend or week out of the trip.
Was in Atlanta in October I think it was - 700 people all discussing SEO, $300 for 3 days of events.
I did do hostingcon2 when it was in Vegas - but after 2 hours, I had met those I wanted to meet and wasn't interested in buying server space through other vendors
I'm all for a weekend trip - get your thinking cap on, and keep airfare prices in mind

Nothing worse than spending more for the flight than you do for the rest of the time you're somewhere. $700 flight, $50/night hotel - not fun.