A few random thoughts:
-- The new modern wing at the Art Institute is finally open, and all reports indicate a great experience (and it better be, considering that it was closed for quite a few years!).
-- A stop-off at Central Camera is worth your time, even if their prices on used gear are off the charts..
--
Vella, beneath the Western/Milwaukee stop on the Blue Line has a stellar breakfast & lunch menu, especially for the veg-only folk.
-- If you're a meat eater, the
Honky-Tonk BBQ in Pilsen has the best brisket in the city, and the neighborhood itself is well worth checking out.
-- If you're a music fan, then a trip to Dusty Groove is a must, especially if you enjoy old funk LP's, and rare, reissued 60's Jazz. For a more live experience, Friday's 'happy hour' at the Empty Bottle (corner of Western/Cortez) is a great time, as the
Hoyle Bros. play vintage 'trucker' country from 5-7pm. If you're a beer fan, plan on taking a cab to and from.
-- The Days Inn at the corners of Diversey/Clark/Broadway has affordable rates, and will put you within walking distance the Red Line (a 10min trip to the loop), a few good bookstores, a nice lakeside park & nature museum, etc.
-- Just my personal, but i'd recommend avoiding Wicker Park like the plague - just another once-worthwhile neighborhood trying to gentrify the world.
Ultimately, it all depends on what you look for from any city that you visit. I tend to prefer the less populated, off-the-beaten-path attractions, which seem to provide a more memorable experience.