Would a roadtrip to Chicago be fun and memorable?
I live in Colorado and have never been to a huge city before and I love to travel. I pretty much live outdoors camping and rafting mountaineering and sleeping in the back of my truck in british columbia, the sierra nevada, and around the rockies.

It will be fun as much as you want it to be, depends on your budget, how you're going with, places you tends going and how long you tend staying.
With proper mind-set you will definitely have fun and be fine! 

It really depends on you. If you want it, be sure to get it.