If they tried to keep me low over the water I'd cancel.
What is "much further north" than VLL direct FEP? Steven suggested BRAVE VEENA JVL, am I likely to get routed even further than that?
On a similar flight I've gotten pushed up to MKG and maybe BAE on the Wisconsin side. I think the routing depends greatly on which flow pattern ORD is using. That ripples out to affect traffic into several other airports within about 50 miles and your routing may take you clear of that. In general, I've found that C90 pretty much dictates what center can do within 50-80 miles of ORD, especially for transient traffic and the routes you get over the lake generally don't accommodate the single engine pilot's desires WRT overwater altitudes and distance from shore.
Subfreezing clouds are pretty much always a showstopper for me. It doesn't matter to me if they're over the lake or somewhere else, I'll be under them, VFR if necessary.
Part of the issue is that clouds along the lakeshore are very common. If you can top them (fairly likely in the winter if there's no frontal activity) it's no big deal but if you have to go under that puts you out of dry feet range for a loooonnng time. My earlier point about ice is that when ice blocks your way across the lake it's quite possible that there's an ice free (and maybe cloud free) route around the lake.
FWIW, even the most out of the way routing you'd get circumnavigating ORD over land will only add about 45nm (about 20 minutes in your airplane) to a direct routing and the difference will be even less if you compare it with a longer non-direct IFR route across the lake. If you go north and they push you up to MKG the southern route could actually be shorter. Finally, if there's a stiff westerly wind up high (also pretty common in the winter and not unusual in the summer), that wind can easily eat well into those 20 minutes going high across the lake vs around the south side.
I understand your thoughts on crossing the lake and for the most part agree, especially if you're not hauling passengers who might not really understand the risk and have made the crossing many times in single engine airplanes (a twin reduces the risk significantly but doesn't totally eliminate it either). I do believe that you are entirely correct about the fact that we pilots face similar risks with far less concern all the time.
And while there are indeed worse things than death, IMO freezing to death in cold water has to be one of the worst ways to die. I always tried to reduce the risk to the extent that I could by crossing at one of the two narrow routes and going very high (i.e 13,000 and above, carrying a raft etc).
Personally, I'd probably go VFR around Chicago between 2500 and 3500 MSL staying out of the Class B. Even if you avoid MDW's airspace completely this only adds about 15nm to a direct route and eliminates going high into a big wind. Coming back, going 11.5 (or higher) over the top of ORD might work pretty well if there aren't any clouds to contend with.
Keep in mind that you can go IFR part way in either direction if you want to get a taste of that as well.
