Nobody mentioned theatre...sigh...

Actually, it's the last thing I'd do for my first trip to a new town, but it does have a legendary store-front, little theatre scene.

I know we all want you to get out of the loop, etc. but don't feel bad if you don't cause there's plenty there for a first trip, but I would head to Wickyland or Bucktown and the aforementioned Empty Bottle or Doubledoor or some such in the evening. If ya'll are thinking of one nice, not too expensive meal, I know some north side stuff but there's probably plenty around your hotel. The good news is you can trip over good places--the bad news is you'll then fall into a corporate place. Just ask around for a neighborhood joint, not a "Let us" place (a big restaurant company here, Let Us Entertain You--they're good, but not what you want for this trip). Folks will know what you mean. Feel free to pm me.

The chicago architecture foudation (they do the "boat tour" folks talk about--don't take the others) run all sorts of cool tours. www.architecture.org/tours.aspx

And, although I'd save the neighborhoods for another trip, just in case you do want to go to the Swedish one, it's called Andersonville, and it's more like 5200 north, Clark and Foster, (the Hopleaf is like three doors south on the West side of Clark but try Konak for unpretentious and Simons for an old neighborhood joint). If you do ride the lakefront path to Loyola, that's a trippy neighborhood, too, and worth exploring. Try the Heartland Cafe there for a big greasy breakfast, even a big greasy vegan breakfast (still, I'd save these neighborhoods for another trip and maybe a local guide...except the Heartland, mmm biscuits).