As a Chicagoan that transplanted 12 years ago from the Pacific Northwest, I can tell you this: Chicago rocks!
No, it's not as beautiful as the Bay Area or Oregon (where I came from). There are no mountains, oceans or many scenic routes. And really, outside of the city itself, there isn't much to see other than malls. BUT this city by the lake is vibrant, fun and offers big city life (culture, nightlife, cuisine) mixed with midwestern friendliness.
Be warned, though: The weather is the WORST. Spring and Fall last are nearly non-existent. The winters are loooooong and dreary. But Chicago summers by the lake are so unbeatable (though, HOT and HUMID) and full of great activities, people are willing to suck it up.
I just realized you posted this question 5 months ago! So... did you make the move?
I think Chicago is a GREAT place tomove to.
When I was first starting out and worked for a tech consulting company, I used to live next to Lincoln Park at one of those highrise apartments (it's been condos for a long time), and just loved it.
People from my company (all single professionals at the time) used to just hop on a bus and go to the Miracle Mile and hangout, it's quite safe around there also.
There are so many things to see and do, cultural activities, fun events, great restaurants, shops, tons of different neighborhoods, great mass transportation, beautiful lake, clear separtion of four seasons; yes, a small New York (I lived i Long Island also); and a very clean downtown (always impresses me). The winter is really not that bad once you are all bundled up and get used to it.
And don't forget the great people!
All in all, some of my greatest memories are there (perhaps because I was young)
Although my husband and I eventually choose to move to Marin, CA, Chicago was on the top of my list to move to. I still have some wonderful friends there. I think you will really enjoy being there!
I hope you're thinking of moving here. I'm a Chicagoan from birth and really love our city. I've written endlessly and posted tons of photos. The link below takes you to all my tours of Chicago and I've posted about a zillion photos of Chicago on my Flickr pages. The blogroll will take you there.