I think the website is the biggest issue for me. When I told my brother who isn't a pinball person to check out what time it started and how much it cost, he had a real problem finding that basic information.
For a long shot suggestion that I understand may not get implemented, I would suggest moving somewhere else. The hotel doesn't seem suited for what you want to do and the space seems limited. There seems to be a lot of options for convention centers in Chicago, surely there's one that would be a better fit. I hate comparing shows but ReplayFX's location looked amazing.