I have a love/ hate relationship with the city. I grew up on the NW side of the city (Norwood Park/ Edison Park). Within a couple of hours and without a car I could go ANYWHERE (either airport, the loop, Evanston, Navy Pier); and I've had more annoyances here and there but in all the public transportation is awesome.
Just recently the city has hit its Beer Awakening. Metropolitan, Goose Island, Piece, Half Acre, and Revolution are all in the city. Another great plus.
It's been said before (and hopefully it will change with the changing of the guard/ Daley), but it's corrupt. And let's be specific. It's nepotism. I grew up in an area where people only w/ HS diploma were city employees and made near a $100k; and the only way to get in was to be a Daley crony. It's hard to believe that so many people are sucking off the city tit that they don't want to see a change, but that's how Daley was able to keep himself nice and secure.
Traffic also blows, but I don't think NY or LA are any better (actually have heard that LA is worse).
I live in central Illinois, but visit Chicago fairly frequently for concerts and shopping and stuff. It's awesome, for sure, and we've had some excellent times... but my god, we've spent a small fortune on parking. Don't park downtown. Better yet, don't take a car.
We also have a thriving music scene. Known as one of if not the best city for Blues in the US. There are several outside venues for concerts and fests during the summer (which is one of my favorite ways to listen to live music) and many venues around the city and burbs from stadium sized venues down to small venues that hold a few hundred people.
Another thing I love about Chicago that people that come from warmer climates may not understand is the change of seasons. It's hard to explain but going through winter makes you appreciate spring and summer even more.Then by the end of summer you almost welcome the cooler weather of fall and the cycle starts all over again. Each new season brings with it a different outdoor activity which gives you something to look forward to as the years go by.
I've never been poorer living in Chicago. I think I had more money when I was in high School living in the burbs working on the weekends.
After you pay all the extra fees to have a car in the city and the fees to park the car whenever you go out, you can barely afford to drive it! I sold my first car because of the astronomical cost but after a year ended-up having to buy another one due to work.
Gas prices are significantly higher here; are we using different gas than other areas? I don't think so, so why are we paying more?
Then there's the rent, you can barely find a decent 1 bedroom for less than $1000 a month. You end-up getting a roommate to save on rent, but still have to live in an area where your car gets broken into every other month even though you have nothing in it.
The job market sucks! I have a Bachelors degree which is useless here. I'm either over qualified for the job or I don't have enough experience. I can hardly even get an interview half the time.
I want to move but I'm getting married soon so I'm stuck unless I can convince the fiance to leave her friends, family, and career. Good luck right!
This city drains you everywhere you look. You can't even go to the beach anymore without having to pay for parking (that used to be free). I wish I never moved to Chicago if you ask me its my biggest mistake.