that's mighty big of you sam. when a tourist asks me for info i just hope i have to piss really bad, otherwise i'll just spit on them.
My grandma went to the Democratic Convention in Boston and spent some extra days checking out the sites and said by far Bostonians were the most stuck up people she's ever dealt with and she's travelled to almost every big city in the country.
I've lived in Houston and visited Chicago and I'll take Houston's muggy summer over winter in Chicago. Now with a few more decades of global warming Chicago may move into the lead.
The winters can get pretty nasty in Chicago, but I much prefer them to the summers. I'm just a cold weather guy, I don't like to sweat unless I'm playing basketball or engaged in something altogether more intimate, and I just like the cold. Even with the lake, the summers are just killers in Chicago.
Houston. With heat you just have to worry about cooling off. With extreme cold, you have to worry about staying warm, worse traffic, keeping snow out of your house, etc. Plus the gangs in Chicago are way worse than the ones here. Oh, and the cost of living.