Not sure why some people have a beef with MDW. Security seems to never be a problem. The number of leisure travelers doesn't seem to be much different from O'Hare. (Even a morning Southwest flight to Tampa seems to be filled with the seasoned 'business' types rather than the leisure and retirement folks.)

Given two flights leaving from the same airport at the same time, the MDW will almost always arrive before the ORD flight. And then have a much quicker taxi. Trip to a rental car is about a minute for MDW, vs. painfully long bus ride at ORD. (I wouldn't be surprized to see somebody be able to fly in to MDW and drive to a hotel in Rosemont before somebody else flying to O'Hare got there.)

Train to city is 25 at MDW vs. 45 at ORD. Food choices at MDW include a number of nonchain restaurants, rather than 20 Cinabons and McDonalds.
Also plenty of local bus service at MDW.