When are you traveling (as in, time of year)?

DEN gets snow.

I'd say it's tight. Your DEN-ORD flight is going to board around 11:05 (30 mins before departure). There goes any chance for overhead bin space.

Can I make a suggestion? It looks like you're headed to NYC, so why not take the puddle jumper from PSP-LAX, then take p.s. LAX-JFK?

PSP-DEN is a L-O-N-G way on a CRJ.