Thanks for the suggestions. Looks like I'll be considering two options:
A) Used Ford Transit Connect from Craigslist - It'd be a tight fit with the things I'm planning on bringing, but I think it could work.
I'd buy a $10k Transit Connect van, use it to drive myself and the dogs and house items (really cram everything in there) and drive to SF before relisting it on craigslist for sale.
Downside: Would need to sell the van once in Cali. Would lose money in the transaction (taxes, registration, plates? What's the most efficient way to do this?)
B) Used a civic/corolla/matrix/vibe/Fit in Chicago and bring a few totes of silverware, clothing items, pictures, etc. In that case the dogs and I would drive together and we wouldn't need to sell the car when we got to SF.
Downside: Can't bring as much stuff. Would need to purchase: Dog cages, small desk, vacuum, other household items that wouldn't fit
I'm leaning towards option B, and selling/donating anything that wont fit.
This might also kill two birds with one stone since I'll already have a "forever car" once I get to SF.
Thanks for the help so far - Mustachians are the best!