C..
I didn't move from Chicago to Houston, but I have lived in both cities, so I can give you my perspective.
First - I lived in Katy, Texas and I also lived in the city of Chicago (Wicker Park neighborhood).
All things being equal - I would live in Houston hands down. it's a much "easier" place to live. But I guess that depends on WHERE you live in Chicago - the suburbs might be easier to live in than the city (where parking is $20, there are few parking lots, traffic is a nightmare etc).
As far as heat.... I guess that's personal preference. I would rather have the heat and a year round pool than the winters in Chicago, which all but do me in. I hate them. I hate shoveling. I hate the whole set up a lawn chair thing. I hate the snowplows that don't plow the side streets until the afternoon of a snowstorm and never plow the alleys. Houston is HOT about 1 month of the year (mid July - Mid August) other than that it's 70-85.for 8 months. Chicago snows from October to April.
Both cities are diverse. Both cities have an urban and a suburban component. Both cities have crappy schools and good schools based on where you move.
The cost of living in Houston is UNBEATABLE. You can get a TON of house for your money. It's easy to fly in and out of there (2 major airports) whereas O'Hare is KNOWN for being crappy, delayed and chaotic.
You have the same stores in both areas. There isn't a "Michigan Ave" in Houston, but there are GREAT shopping malls. Woodlands is fairly equal to Woodfield. Houston Galleria has the same upscale shops that you can find on Michigan Ave.
So, to summarize: Houston, Houston, Houston, Houston, Houston, Houston, Houston, Houston. Houston. :-)