Congrats to your newly wed son! I'm sure you're starting to contemplate the move to perhaps move closer so that if the idea of grandchildren comes up; you won't be too far away? If so, I can identify 100%. I moved down to the fantastic city of San Antonio 9 years ago from Indiana. All of my immediate family still resides up there, so every year they have to fly down once or twice (or vice versa) to see our children and family here.
Obviously the major difference is weather. The normal cold down here for us can get as low as the low 40's at night and then warm right back up to mid 60's and low 70's by 4 pm. The cold snap may last for a combined 2 months if that. It really starts to get toasty around March, April and then won't stop until late September, October.
Driving is a HUGE difference too. We have "frontage roads" throughout and everything is much more spread out here than up North. The traffic really isn't bad compared to inner Chicago at all, but since everything's so spread out; it may still take you the same time to get from A to B because of distance.
If you would be needing to find employment; our economy and job growth for the area has still pushed us to healthy levels as we are having more and more major employers move into our great city. If you would like to know more about SA's economy at a snap shot: copy and past this link here. http://www.bls.gov/eag/eag.tx_sanantonio_msa.htm
There is so much to do and enjoy here in San Antonio. If you are looking for outdoor activities; the list goes on and on. If you do ever need more specific information; I'm sure you can talk to any great Realtor here or even your son; so I'll just end this by telling you a fact that I find most important about this city. San Antonio is the 7th Largest City in the US, but you almost could never know as the people here are by far the most friendliest you can find. It's a large city with that small town feel! I love it!
I was born and raised in San Antonio and will be more than happy to assist in any way I can, give me a call @ (210) 422-6293
I'm not familiar with the tax structure in IL, but in TX there is no income tax (maybe not a major factor if you're retired) but high property taxes compared to most income tax states.
I've known a number of folks that have moved from the mid West (primarily St. Louis) and most have enjoyed the area and stayed. We moved here from St. Louis 14 years ago and fall in that category. Those that moved back tend to have lots of family they left and return for that reason.
This is a tough thing for a real estate agent to say, but you would may be better served renting initially until you're pretty certain the stay in San Antonio is long term and to give yourself a chance to see if the area is for you.
I'd be glad to respond to specific areas of concern on this forum or via my website!