I’m back from a very quick trip to Chicago and, believe it or not (I don’t), it was my first! I am barely allowed to have an opinion, but since I have a blog… I WILL! (And please share your opinions, too.) 
A bunch of people have asked me what I thought of the city. Let me preface this by saying I have a LOT more to see and learn! But we’re all entitled to first impressions, right? (As long as we’re willing to be wrong…)
I will say that, despite the rumored cold (it was surprisingly comfortable for a January weekend while I was there, probably no colder than 20 degrees), despite the generous dose of grey (I did have one beautiful day of misty sunshine!), and despite the sloppy leftovers of post-holiday snow patches on the sidewalk, people just seem to love this place. I can understand why.
This is clearly a proud city, but it’s not obnoxious-proud like Boston (sorry guys), or stuck-up-proud like New York (I still love you NY!), or chip-on-its-shoulder proud like Philly (eek… this is going to bite me back)… [And for the record, I really think Boston, NYC and Philly are awesome places.] It’s just hey – let’s bundle up, go eat, watch a Cubs game, and grab some beers-proud. Maybe I haven’t spent enough time in the Midwest [fact] to appreciate that sort of simple, friendly charm (yes, sometimes friendly cities confuse me a little) but Chicago is as tough as it is charming. Kind of how I like my men. (Umm…) It’s got the boxy build of a warehouse-meets-high-rise, yet it’s comfortable, modern, breathable and fresh.
Chicago Architecture
Every city has its tough days and its glory days, but Chicago seems to focus mostly on what to eat today. I like that it’s got a no-nonsense vibe. Much to my delight, it is a foodie city. For the most part, it seems to have fun with grub. People go out to eat so that they can enjoy a place, not pick it apart. The food-culture is unpretentious yet informed, familiar yet refreshing. Even with such an amazing selection of restaurants and bars, residents find themselves settling on a couple local favorites where, before they know it, the owner is showing them photographs from her freaky 80’s prom-hair days, and making fun of their dates while a nearby group of diners looks on and laughs.
I’m under the impression that Chicago is also a beer city, and a coffee city, and a sporty city, and, well, a happy city… Yep, pretty much my kind of city, except for the whole cold thing. But the cold is bearable thanks to the awesome people, who seem constantly upbeat and pleased with Chicago despite the low temperatures. I picked up on their strategy: never lose sight of summer, no matter how far away it might be.
Chicago View
Every Chicagoan asked me how I liked their city (even if I had been there less than a day). After telling each person my positive first-impressions, I was consistently and continuously reminded of one thing: that I absolutely HAD to see Chicago in the summer time. (Is this a trick?!) These poor people don’t even realize that summer only lasts three months, and that’s what’s so cute about them — it’s all they need!
Ahh, I love their optimism. Those summers must be pretty awesome if it gets them through the other 75% of the year! Maybe the winters aren’t that bad after all…
For the foodie culture, the just-beautiful-enough streets, the variety (be it food, beer, ways to pass a Saturday afternoon), the blending of architectural styles, the pedestrian-friendliness, the positivity, the cleanliness-mixed-with-Brooklyn-esque-grunge, and sure, for the constant availability of cabs… I give Chicago two thumbs up.
Yep, even during the winter.
Travels with Tavel 
I like this one. Really captures the feel of the city. And it is great in the summer time. This past July, my friend and I biked into downtown along Lake Shore drive on a gorgeous, gorgeous afternoon. Water on our right, skyline silhouetted against the blue sky in the distance. Really nice. And I agree that it isn’t arrogant, obnoxious, or have a chip on its shoulder like some Northeastern cities. Just a nice big place with plenty of great food.
I am starting to think that Chicago might just be my kind of city. Rachel you make me want to hop on a plane and get my ass over there to check it out. It sounds like Chicago is a friendlier and more spacious version of New York.
As an obnoxiously proud Bostonian (really I’m more obnoxiously proud of Worcester) i felt that I needed to comment on this one. After having lived in Michigan for a year and a half, there really is something to the “midwestern” charm and niceness that doesn’t exist on the East Coast, which would definitely explain why the Chicago proud isn dissimilar to that of Boston, NYC and Philly. I’ve only been to Chicago once in the summer for a wedding and I have to say the idea of a big city with a large beach right in the city was awesome!
Chicago sounds much more interesting than I had expected. Those skyscrapers are fabulous!