MDW has its points, but even though it is 15 minutes from my house, I'll drive 20 or 30 minutes to ORD.

My experience is that airports with high volumes of leisure travellers are a PITA to deal with. Nobody knows how to deal with security checkpoints, they are all lost, and they like to stop in the middle of the concourse and dig through their oversized carry-ons.

I hate SW. I want to know where I'm sitting and I don't need games on the plane.

Also, in my experience, baggage claim at MDW is about the slowest out there.

As for driving to Milwaukee from MDW in two hours? Sure. As long as it isn't rush hour or a Friday in the summer -- or any time it snows. I've spent 90 minutes getting from I-290 to Half Day Road plenty of times. So yeah, if you have control over timing and you can get to MDW mid-day or late at night, two hours of driving is a possibility. For the rest of us, I'll take the extra segment and 500 miles. I like MKE -- it is a very nice airport. They even publish a comprehensive timetable http://www.mitchellairport.com/MILAPT0001.pdf

Heck, if MKE is your final destination, why not fly Midwest Express? Frontier connects through DEN and NWA connects through MSP. You've also got America West through PHX. Lots of options to avoid ORD. Somehow, SW to MDW would be last on my list.