The new Midway is great - but it's also a victim of its own success. It had the misfortune of being designed and constructed largely before the 9/11 attacks. The architects made a huge mistake in siting the security checkpoint on the Cicero Avenue bridge, IMHO (although they had no way of knowing what was about to happen).
The Chicago DOA has done its best to expand the checkpoint, and now it fans out into the middle of what was supposed to be a vast, open airside lobby. Arriving passengers going to baggage claim get funneled through a narrow passage into the landside terminal. There's been talk of building a second security bridge, or widening the existing one, but both prospects are very expensive and not likely to happen in the next few years.
To me the new MDW
is too claustrophobic. The gate areas are wonderful and HUGE improvement over the old concourses, but the landside terminal, baggage claim and security checkpoint are just as much of a pain as they were in the 1947 terminal.