Thanks, everybody, for the advice and the new ideas.
Main consideration is time: I'm going to be rendezvousing at SFO with mr. hollander, who will be getting in from HKG at around 8:30 a.m. Via ORD I can get there at 10:36 a.m. and via DEN at 10:15 a.m. (theoretically). Would like for him not to have to wait too long for me.
I'd be okay with the regional jet to DEN, as it has E+; and I've lived through so many UX cancellations or massive delays to ORD that I'm wary.
On the other hand, maybe I should stick with the devil I know.
On the fare: they're both coming in at just under $700 for the times I need - sticker shock for me.
Thanks again for the input - I appreciate it!