What size kites do you currently have and have you been riding in Chicago for a while? Kiter sizes can vary greatly depending on the season and time of year. I'm 200 lbs and amazed how often I ride my 6m SS Rally each year. That being said, you can't go wrong building a quiver of kites around a 10m - 12m size as the first kite and then go up or down on sizes depending on season.
Are you firm on North? I used to be a North dealer, but had some quality issues, but that was many years ago. Do you have a riding style yet? Freeride (cruising and big air), Freestyle (aggressive and unhooked riding), waves?
I'd be glad to help and of course the best place to buy is Kiteriders in Madison. I've been in this business for a long time and know the importance of having a local source for service, etc.
You ever get up to Madison?
Take care and good luck. You can also contact me via firstname.lastname@example.org
or 608-358-0514 cell.