I have a 35 minute connection in ORD for my DTW-ORD-LAX-PDX-GEG routing in Sept. DTW-ORD arrives at 6:55am and ORD-LAX departs at 7:30am.

Yes, it would probably stupid to book this connection, but GEG isn't the easiest airport to fly to in terms of price or availability. I got a great fare and lots of miles out of this one.

Should I even bother checking a bag? I don't see how it possibly could make it onboard in ORD on time. I would like to bring some items (camping equipment) that aren't legal to carry on, so checking is preferable.

I've actually never been to ORD but have heard the nightmares. I intend to sprint through the airport if necessary to get myself on the flight to LAX.