Seeing as Phobos and I live here, the biggest limitation for us is work, but if we're planning this far in advance, I'm sure we can arrange time off. {= )
Also, assuming nothing is drastically different next summer, we can possibly even offer accommodations for one to four people if you trust us and we trust you. {= ) We have a day bed with trundle for one to two folks (if they don't mind sharing a room) and a futon sofa for one to two more (if they don't mind sharing a bed). Note that we are up one flight of stairs and will almost certainly have a cat by then. Also, we have only one bathroom.
But that would help some of you with the biggest constraint, which is money. Travel and accommodation are probably going to be your biggest expenses.
If you're not up for staying over at Chez Nesh, I understand there are good hostels in the area, or you could get a less-expensive hotel somewhere in the Greater Chicago Area and take the Metra to and from the Gathering. That's what my dad and I did for the 2006 Chicago Gathering, when I was still more comfortable being accompanied by a parent. ^_~ Once you're in the city, you can get pretty much everywhere by train or bus, and I recommend that over driving by far. Weekend passes are useful and far more reasonably priced than parking in a garage or something. But if you insist on driving, check out SpotHero for some options off the beaten path that may be less expensive.
Fortunately, there are things to do around here that are free, such as the Lincoln Park Zoo, music and plays in Millennium Park, and various festivals. This page lists free and low-cost events for this summer, just to give you an idea.
And, since museums are a Gathering staple, here are some free and low-admission museums to consider. The only one I've actually been to is the Nature Museum, so I'd be up for checking out any of the other ones. 'Course, with a year to save up, the bigger museums are certainly not out of reach. The Museum of Science and Industry, the Field Museum of Natural History, and the Shedd Aquarium are all awesome.
I'd also like to put in a good word for the International Museum of Surgical Science, one of our hidden gems, which is $17 for adults and $13 for students at this time—but I know that's not everyone's cup of tea. I just found out we have an American Writers Museum, though! I feel like that might be necessary. And it's only $14 for adults, $9 for students!
There's also just getting together and playing board games and stuff in person for once, too. We have some good ones! {= D
~Neshomeh