To start with, I generally travel light once I am approaching security. There are several reasons for this. First, I don't like lugging a bunch of stuff through the airport. Second, I don't like the amount of stuff people shove into the overhead bins, so I protest by putting as little up there as I can. When I'm traveling with a laptop, I would have to have my laptop case, my CPAP, and the rest of the stuff I need for the trip. If I'm not taking a laptop, then I only loose the laptop case. So I've taken to always checking a bag -- unfortunately usually my largest bag since I holds the CPAP case inside instead of having to carry it or check it separately for $25.00.
This leaves me with just what I'm wearing, and one carry on bag which is either my laptop case (a backpack most of the time) or my sling bag. In this will be the stuff I need on the plane (reading material, iPod, headphones, etc.) and stuff I cannot check (liquid medicine for my nose and sinuses). To make things easier, I try to put my coat, if I'm wearing one, into my checked bag so I don't have to carry it through the airport, nor worry about it while flying.
Next, I've taken to wearing a pair of clogs (Crocs) when I'm flying. If I'm flying after church on a Sunday I will wear the flat black Disney ones with black socks, which makes them look sufficiently like black shoes that few, if any, people would think its strange. On other trips, I've got my choice of two pairs.
Finally, before I ever get into the security line, I empty my pockets into my carry-on. I put my watch, cell phone and belt in there as well. When I get past the first screener, who checks the ID against the boarding pass, I remove the holder around my neck with the ticket and ID in it. When I get a chance, and am close to the head of the line, I remove my shoes and the 1 quart bag with my nose spray. As soon as I can, I grab two bins, put my shoes, 1 quart bag and ticket holder (without the boarding pass) in one, and either my sling bag or the laptop in the other. If I'm carrying the laptop, I usually let the case go through without a bin since it is sturdy and stiff.
Recently, I've been able to -- or more correctly had to -- go around someone who is fumbling with their shoes or belt. I don't think I've been delayed by this strategy except for last Sunday when I had my keys in the carry-on instead of the checked bag, which forced it to be hand checked.
Add this to printing my boarding pass ahead of time most of the time, I've actually gotten to the point I usually have lots of time inside security before my flight. Not that I'm going to start getting to the airport -- especially O'Hare -- any closer to the flight, but it is nice to know that I'm usually safe.