I'll bet you're paying as much in Lombard as you would in Lincoln Park/Lake View/Wrigleyville. You can over pay in either place and it's a misconception that the rents in city are a lot more then in the burbs. The difference is you get a little more space for your money. The other difference is that you have to drive everywhere if you live in the burbs. I haven't owned a car in almost 10 years until this year. So 400 per month times 10 years is a lot of money I didn't have to pay because of living in the city where a car is not needed.
Out in the western burbs it gets a little more hilly but for the most part its flat as a board until you go out west near Rockford/Galena area or North towards Wisconsin/Illinios border it gets more hilly. South towards Starved Rock (2 hours SW) gets a little hilly as well. Anywhere near a river it gets a little hilly.
The weather differences between NC and Il is that it rarely snows in NC you get a lot of ice and the humdity is very high in the winter making it feel colder then it really is. Illinois the air get really dry making the cold not that bad if the wind isn't blowing. Which isn't very often. The only thing your dog is going to notice is their isn't many pine trees to piss on.
Not too many 50M pools in the area check out this link to find what's available
http://www.swimmersguide.com/query/Search.cfm Oh a friend of mine from High School when to Carolina and lives in Naperville. He gets together with all you blue headed freaks for basketball games on TV and to watch the tar heels get a drumming at football. I'll never understand it but if want to know where they meet in that area send me a PM I'll see if I can find out where those misguided souls meet.