I know that I just posted a new list but I had started that list a long time ago so it doesn't really count as today. 
Reasons I like Chicago: (In honor of my current trip to Chicago.)
1. Walking.  Every time I go I either walk or take public transportation.  These win huge brownie points with me.
2. I like the people I know who live there.  This may rank as most important if I were to rank these lists.
3. Tracy's Apt. One of the wonderful people in my life who calls Chicago home has a great apartment at Washington and Halstead on the 34th floor with 2 walls of windows that look over the city including the Sears Tower.  I got to see lightening strike the Sears Tower last night. :)
4. The pizza. 
5. The weather.  This one is weird but I like that nearly every time I come to Chicago the weather will be different.  It does make life exciting.
6. The tourist stuff is largely close to each other.  Goes back to the walking idea, but I like that in a city this large you don't have to drive to each tourist attraction.
7. Carl Sandburg wrote a poem about it.  I know, I'm a nerd about English stuff.  I'm also a nerd about things that relate to buildings or pieces of my childhood (like Abraham Lincoln) and I went to Carl Sandburg Elementary. 
Anything else I like about Chicago is largely just what I like about big cities.  I don't end up spending large amounts of time here so that limits my ability to get super detailed and I'd put theater on here but second city is stationed in a lot of places and I'm sorry but The Fox in St. Louis blows away any theater building I've seen here.  The city does have its perks though.
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