-- Love architecture
Unfortunately, Chicago had little interest in preserving its great architecture, but -
Check out the Frank Lloyd Wright buildings in Hyde Park and Oak Park (the latter a short ride via train or El)
The "Chicago Cultural Center" (used to be the main public library - great interiors)
Carson Pirie Scott facade (now something else) State & Madison streets
Stock Exchange trading Room (now preserved inside the Art Institute of Chicago)
Sullivan's Auditorium Theater (there are tours)
I wouldn't really say "little interest" so much as it all burned away...
Pizza you go to Lou Malnati's. Fun things to do: Navy Pier, Boystown, Willis (Sears Tower) or John Hancock. You mentioned cocktails, go to the Signature Room at the top of the Hancock for a night drink.
Whirly Ball is fun, we have some cool Arcade Bars or Dave and Busters. We have some cool Lazer Tags and such. Grab a show and see if any local bands are playing! Go to the museum campus if you dig that stuff, the Adler Planetarium is awesome, as is the Mueseum of Science and Industry and the Museum of Natural History. I'm not a fan of the Shedd Aquarium, but it's tops if you like captured animals! =/ Eat a Chicago Style hot dog and if you come soon, see a Cubs game (who cares I don't much like sports, but it's an essential part of our city and Wrigley is beautiful) Try the Botanic Gardens in Glencoe up north. Plenty to do here, just need to find what interests you most! Send a message if you need. Will be glad to help you out!