Chicago is a great city. Unlike New York, LA, Boston, and Philly (and from what I've heard, Atlanta, Houston, et al.), you can actually drive around without too much hassle. It's a "manageable" city.
Taking the CTA from O'Hare to my friend's apartment was a breeze, and only cost $1.50. The same trip covering the same distance in New York would have been more expensive and would force you to change trains at least twice--a complete pain the ass.
Since Chi-town is a midwestern city, the people are a little more laid back. But that can also mean they have no freaking idea how to drive.
There's a lot of young female ass walking around the city. One particular bar, Kincade's, was stocked to overflowing with it. It was the same the last time I was there, in 1993 (when the Knicks' Charles Smith was having point-blank shots blocked at the end of that Game 5 loss to the Bulls). Only the problem is that I keep getting older, as they stay the same age. I felt like an old pedophile just having a couple of beers there.
Whole Foods has a great beer selection. I just don't know if I'm ready for the Golden Shower.
If you walk into a massage parlor with another guy, there's a good chance the receptionists will look at you as if you're a couple. Not that there's anything WRONG with that.
A lot of people were wearing those annoying Bluetooth hands-free earpieces for their cell phones. All I can say is: get used to it, because everyone will have these within a year.
Northside Bar in Wicker Park, is exceptional, with a nice inside/outside setup, cute female waitstaff, decent prices, and HD screens. But the Map Room on Armitage had the most incredible beer selection, with countless beers on tap and in bottles. (Actually, "countless" is not a correct term, since there was a finite number of beers; I just didn't feel like countning them. It was a whole lot.) I think I had the Ayinger Braü Weisse, but I can't be sure . . .
Band of Horses is an excellent band, with a bad name. They're not from Chicago, I just wanted to mention them since I first heard them on my friend's iPod on the flight over.
Cardinal Zin, a zinfandel from Bonny Doon Vineyards ($18), is an excellent wine for the money. Again, not from Chicago, but I drank a lot of it there. This was the first bottle I bought that had a Stelvin enclosure (it sounds much cooler than 'screw cap'), which helps prevent cork taint. Hey, anything that helps you get women drunk faster, I'm all for it. Oh, and I just wanted to say 'taint'.
A simple brunch can cost $40 a head, if you order the most expensive champagne. Twice. Yeesh.
Finally, never take a trip to Chicago with a vegan. I made the mistake of going with a friend who is a semi-vegan (doesn't eat meat, but some dairy and fish), and all that time in Chi-town without eating a steak was really a bummer. Plus, the menus filled with "tofish", "seitan" and "eggz and hamm" just pissed me off after a while. It's too much work being a vegan. I ate a turducken, with veal and pork stuffing, and a taco salad as soon as I got home.
Favorite T-shirt: "OZZIE [GUILLEN] IS MY HOMEBOY".