I haven't watched the video, but based on the comments above, it's clear this guy either didn't have a set of "Personal Minimums" or just ignored them. The day I got my license (1993) my instructor reminded me of the minimums he set for me during my cross-country training. We talked about the "License to Learn" and I set 3500 feet and 5 miles as my minimum for departing my home base pattern. I plan my cross-countries keeping those minimums and create a "trip book" with all the airport facility guides that cover my route. As I fly along I will dial up the AWOS frequencies to stay alert to the weather ahead. VFR pilots should be looking at the big picture regarding weather for several days before any planned cross-country. You just can't have too much information regarding fronts, cloud cover, winds aloft, temperatures, and pressures. I would not fly a long cross-county at or near my minimums, I look for improving conditions along my route or just wait until the weather move out. I am familiar with the area west of O'Hare, there is a VFR "corridor" through the west side of that class B airspace that passes about a half mile east of DuPage. You can get an ATC clearance through there "at or below 2500" and will be instructed to contact DuPage tower before entering that airspace (Class D). I know of no low level obstructions in the area, but it is a well "developed" urban landscape, and if your going to fly through any Class B airspace you should have a Terminal Chart along and hopefully have reviewed that chart before departing. There are a lot of airports along that route which takes you north through the Class B to Wisconsin. It is really sad to hear of yet another avoidable accident killing a family.

Joe