Originally Posted by
blort
The only way I see you pulling this off is if you can walk to your office from the train station (or your employer provides a shuttle) and you live somewhere like Logan Square, which lets you walk to the Healy station on Metra's Milwaukee District North line.
+1 for Logan Square. It's also close to the expressway and you can get more apartment for the $$$ than you can in Lakeview.
If the OP is set on City living, then River West / West Town (near Ogden/Chicago/Milwaukee), Wicker Park and Bucktown all have relatively easy expressway access...though you're still probably looking at 45-60 min commute.