Going to Chicago was one of my first trips really traveling by myself--in all other trips I either go with a friend or my family, and even though Lauren lives there, she had to work during the day on Friday so I was left to my own devices. Surprise surprise, I liked being alone! When you go around to tourist attractions and museums, its nice not to have someone following you or nagging you about stuff. And being the planning neat-freak that I am, I made a list of all the places I wanted to visit and foods I wanted to try. And I printed it off and crossed stuff of as I did it. Obviously.
Speaking about the city in general, I loved it. The people were friendly and the city was clean and easy to navigate. The only negative was that the public transportation was nowhere near as proficient or all-encompassing as NYC's. And I doubt I would enjoy their winter's. But I would definitely say that I would go back!