Answers:
Ursula Haigh
Burien
You run the risk of missing your connection since you will be required to go through a security check again. Depending on how far you want to go, it would be a gamble with traffic.
vivacekate
Chicago
You could try, but it would be a risk. Security checks out and back in can take quite a while, so you would at the very most have a couple of hours outside the airport.

