It made me

overjoyed!

How I did it: I was invited to a wedding about an hour outside of the city (one of the girls I did my semester abroad with, I hadn't seen her since the last wedding a few years back.) And since I'd never been to Chicago, I took a couple extra days off work to check it out.
I got ftickets through Southwest, which were cheap, and the experience was pleasant and reliable.
I spent the time before reading a travel guide, taking notes, making copies of maps, etc.
I set up reservations at a cool looking hostel, as well as car rental and hotel for the wedding in Sycamore.
Public transportation there is awesome! It's easy to get around, seemed fairly clean/safe. And for me, was very exciting! I walked a lot too.
I really wanted to get s sense for what it was like to live there... and experience it for the 'tourist' reasons too.

Trip Highlights: (in somwhat chronological order)
- Lincoln Park. This is the area the hostle was in. The Park is great, and the (free) Zoo was awesome! The neighborhood was so-so, but proved fun the night of hte hostle-led bar crawl.
- The Getaway Hostel. Very awesome, definietly recomend this one. Clean, funky, fun.
- The Art Institute of Chicago. It's the 2ND largest art museum in the country... and it's pretty amazing!
- The Bean. I spent at least an hour there taking pictures.
- The Searstower View. I went at night, which was gorgeous.
- FOOOOOOD. 'Nuff said. Yumm!
- Funky neighborhoods. Street art. Awesome shopping. Read how I did it… 14 months ago