As a Cheesehead who moved to California 16 years ago, I've used ORD on many returns to Milwaukee. No more. Even when everything was on schedule, going from Term. C to E/F was no fun. Add in the terrible delays we've seen in recent years and, just as important to me, the overcrowded stressfest that is Term. E/F, and it's pure misery.

Last trip home, I flew on Southwest to Midway -- what a nice airport! I could walk over to the rental car (no bus), get on I-55, I-294, I-94 and arrive in Milwaukee about two hours after flight arrival (with fairly slow traffic getting out of Chicago). That's about the same as when both legs of a fairly tight ORD connection are on time.

Anyone else buying MDW and selling ORD?

no way, MDW is still a ****hole but if it makes you happy then go for it ^

I'll give you that MDW is easy to get around, but the drive there is so depressing. 55 and Cicero, ugh. And now Cicero is under construction which makes it even worse.

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.

It was so simple for many years -- SFO to MKE nonstop on Midwest. Those days are over. They now have connecting service through Kansas City. The only nonstop option now is SFO-ORD or OAK-MDW, with a drive.

MKE is indeed a terrific airport. If anyone offers nonstop service from SFO or OAK, I'm on it. Until then, however, I'm driving from one of the Chicago airports -- MDW in all likelihood.

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.