William, I have 15 years living in Chicago overall with the last time being a year in 2003-4. Since then the sales tax rate has gone to the highest in the country at 10.25%.
The overall tax rate is high in Chicago. For instance, when I went to get the required city sticker for Chicago proper it cost me $150 in 2003. I was paying $85 I think it was for the same sticker in Houston. The State of Illinois is broke, and considering raising the flat rate of 3% State income tax to 4.5% or 5% soon because of it. The city of Chicago will nickle and dime you taxwise to death you'll find.
Crime in Chicago can be a huge problem visiting unknown areas. High crime is just a fact of life in Chicago, although there are pockets--particularly on the North side--that are very safe. This is easily checked on the net if you plug in something like "crime map Chicago" in the search column.
If you have a condo there, you won't have to worry about shoveling. Same with apartments.
Public transportation is super-excellent, and you can go anywhere you want 24/7 in Chicago on it. Many, many innercity Chicagoans have no car at all, and don't need a car there.
The people in Chicago are straightforward and direct (too direct for some, I'm sure), but, personally, I really love it's people. Not especially friendly towards strangers, but, if you know someone they know, you're in totally. Chicago has always had so many transients there that they are pretty sophisticated. Everyone is accepted, and I mean everyone. You shouldn't have a problem making friends there at all, really, if you just put out a slight bit of effort as people there aren't hard to get to know. They just aren't going to go out of their way to meet you is all I mean (too many people coming in and out).
And realize that Chicago is THE most segregated city in America: the young/hip live together, the Polish live together, the Asians live together, the old rich live together, the Blacks live together, the Irish working class live together..well, you get it. At least you'll know where to go to get good soul food or good Irish beer. Just realize that this city has always been this way, however, everyone seems to get along with everyone else there. No race riots or problems like some cities have had in the past.
Chicago's a totally Democratic town, so, if you are of a different party persuasion, you may find yourself in the minority if this is an issue with you. However, the Independent Political party is very active there still, so if you want to remain neutral there's a place for you politically to go.
Chicago offers so many sports, cultural, educational and social opportunities that it's amazing. And it is now considered the best restaurant city in America (over NY and San Francisco). You could eat 365 days a year at a different inexpensive mom and pop place that was delicious. I love this about Chicago!
As for me, the high cost of living, the cold, the taxes and the high crime stops me from retiring there. I love Chicago...but I'm sure I could learn to love somewhere else just so well as Chicago.
**However, if I did decide to retire in the Chicagoland area, I think I'd keep my car and buy somewhere around Crown Point, Indiana, or Valparaiso, Indiana--both a short train ride away. It's safer and a calmer lifestyle over there, but you have faster access to downtown Chicago than if you lived in the northern suburbs! To me, that's the best bet!**
