Closest airport is Midland
Start at Homer Wilson Ranch, go up Blue Creek into the Chisos; do the rim, Boot Canyon and Emory; go down Juniper to Dodson trail back to Homer Wilson.
Then, head west to Big Bend Ranch state park--it is epic!
If you do the Guads, I'd do them first--just go to Pecos, head north on 285 to Orla and hang a left on 654--one of the more scenic hikes in Texas; Guad peak is a dayhike; also, if you haven't hit Carlsbad Caverns, it's only 40 miles north.