Wildly variable. They've started cutting back on the random selection of people for PreCheck, which at one point was about 50/50, but I've never had it take more than 10 minutes to get through.

I also don't think it's going to take you 10 minutes to get to the Orange line, unless you're planning to walk across the Loop, as you can get on a block away at Quincy, but either way walk + L shouldn't take more than 35 minutes, accounting for congestion around the loop. I think 7 minutes is a fair estimate station -> security if you walk at a brisk pace and carry bags up/down stairs.

Bottom line, if I knew my feet were hitting the sidewalk at 5 on the dot, I would do it myself, but keep in mind there is little room for error.