Hi Adrianna,
Have you had any more thoughts on your Routes and travel times that have been mentioned?
I am sure there will be more help available here but it would be an idea to share your thoughts and possibly post an outline plan up and then we could possibly recommend places within your schedule.
With 14 days I would be looking at 6 days travelling from Chicago to Vegas and back and with 4 days in Vegas and 4 days to L/A and G/C pretty much takes your time up but allows time to make stops in Dallas and Memphis e.t.c.
Is L/A a "must do" this trip? It would free up a lot more time elsewhere in your travels.
If so what are your interests?
I hope you have a great trip!