I've never been to Chicago... but my friends have all said it's kinda boring for those that just want to casually socialize and play free pinball. If you want to be close to the industry; Chicago is the place to be.
If being social and free pinball for three days is your motivation; Texas Pinball Festival is your place. I personally spend a lot of time prepping my machines for it... along with onsite repairs to keep them running. Many others do it too. *AND* they don't close early like the Chicago show Mike was biasedly pimping earlier.