For pick up... I love Chicago. I was able to get really good really fast because I was able to practice so much. There are clubs/bars/lounges EVERYWHERE out here. Literally, you can completely wreck a whole bar and just walk 500 feet to the next place, and get a fresh set of people who have no idea how big of a fool you made of yourself at the last one. It's called the Windy City for a reason... There is a ALOT of shit going on out here. Even on Monday night (personally my favorite night of the week to go out... Industry Night. That's when all the strippers and gogo dancers come out to play

) there is alot of shit going on. You can ALWAYS find something to do.
But here... You've gotta be one COLD mother fucker to live in Chicago. The people here aren't as friendly as they are in other states. Everyone is so busy and has their head so far up their ass, its not an easy place to learn your way around unless you know someone. People will act as if you are fucking up their whole day if you simply ask for directions. The cab drivers out here are like terrorists in training the way they drive. You are pretty much guaranteed to catch some type of disease if you lean your head against the window on the red line. The police suck. There are double digit shootings DAILY. The public parking is ridiculously expensive. Don't expect to pay less than 25 dollars for a long island. The summers here are brutally hot and the winters are outrageously cold. There are 2 seasons here... Winter and Road Construction. (Which means traffic is always a bitch.) A pack of cigarettes costs over $10. Sales tax is 10.25% on everything. And the part I dislike the most is the fact that I've had more bums in the Gold Coast fuck up my sets during street game, begging for change, than I have had anyone else lol the Gold Coast is one of the nicest parts of the city and they have now wandered their way into it.
Chicago used to be a great place to live. Tons of street festivals and shit... But the city has pretty much gone to shit now. It might be my view on it because I've lived here my entire life. So I will say if you are interested in a new experience, definitely check it out. But I will not be here much longer lol
I will agree with the above posters about Denver... BY FAR the nicest, friendliest, most welcoming city I've ever been to. The population isn't as big as Chicago and the bar scene is nowhere near the same.. but you won't have to worry about getting shot when you are smoking a cigarette on your front porch.