...it looks like the taxes will possibly get even higher in IL based on the budget standoff between the Governor and the State Legislature (and they're all Democrats...unbelievable!)
If your kids have plenty of room for Grampa and Gramma to visit, check out the air fares between Orlando and Chicago (or Orlando and Milwaukee if you live north, or Midway if south). We don't hesitate to fly more frequently than we might given the cheap air fares to and from Orlando. This year we're flying up for a four-day Thanksgiving, then again for Christmas, then to New York for a neice's wedding in mid-January. Spend a few minutes on
Kayak.com to check out future fares.
All told, for my wife and I the air fares for those three trips totals not much more than $1,100. The long-term off-airport parking at Orlando is only about $7 a day. So calculate a few trips back to Chicago and then figure that as a percentage of the taxes, insurance and utilities on a second house in Chi town. Then there's maintenance--something will certainly break whether you're there or not.
Good luck with your decision. One thing is for sure--there are plenty of brand spanking new houses available for immediate move-in here in TV. On my daily bike rides, I see whole blocks of empty houses in and around Mallory Square (south of Mallory Hill CC between O'Dell and Morse). And from what people are saying, maybe even a break from TV management. Might as well ask.