Chicago is nowhere near as high cost-of-living as NYC/SF/LA. A modest house in a nice suburb near mass transit, or a condo right in the middle of downtown, can both be had is the $250,000 range. A modest but lovely 1 bedroom condo in the same nice suburb can be had under $100,000, and would be perfectly suitable for a retired couple. In many other big cities, it's hard to avoid paying a lot in rent/mortgage without making huge compromises like a brutal commute or a very dangerous neighborhood with bad schools, but in Chicago, that just isn't the case.