Dang it, Mike!
Please never go to Chicago. The hotel costs alone would kill all game buying budgets.
We went to Pokemon Go Fest in Chicago in 2017, and Harry Potter Wizards Unite Fest in Indy this year. It cost us $109 for the Westin in Indy, and would have cost 3 times that in Chicago. Now inflate that for Gen Con prices and it would be insane! Its already over $1000 for a DT hotel in Indy, it would be over $2000 for a hotel in Chicago. Plus Chicago wouldn't roll out the red carpet like Indy does. We come from Detroit, the drive is probably the same or shorter to Chicago, and I would much rather stay in Indy.
Everyone will never be happy with everything, but Indy does such a great job. Even when we went for HPWU it felt more welcoming than POGO in Chicago.