All,
I have commuted to MDW for a LONG time.
The crashpads are plentiful. The advantage is it's a 10 - 15 minute walk from the lounge to most crashpads. Though even that seems long in the winter! There's no worry about transportation or hotels filling up. Most of them are pretty clean and include cable/internet. Usually 2-4 to a room with your own bed. I rarely share my room.
The hotels are a pretty good deal as well. I think the Holiday Inn is about $75 out the door (brand new hotel). Right now they are always available, however I did the hotels several years back and they were filling up occasionally.
Overall a great base with good people and great Chief Pilots. Looking forward to putting this behind us and kicking some butt.
My personal feeling is this passes by 70-80%.