Well, having flown from Chicago airports for years, I can chime in on the subject:

1. I avoid MDW like the plague. Primarly due to the nightmare of getting to and from MDW from the NW suburbs. But, if you are in the SE burbs or downtown, MDW would be more convenient.

2. The larger issue for me though is the miles. I should aask, where do you want to do with teh miles. If you say anything beyond our borders, then WN is a waste.

3. Hit CC and see if acquiring 2P status is available to you.

4. Avoid the cattle call. Check-in 24 hours in advance at united.com and pick your seat.