Here's a suggestion for a day in the Windy City:
Start out by eating breakfast at Lou Mitchell's on Jackson, in the Loop. You'll get no frills, just really, really good breakfast food. FYI - they don't take plastic, so bring cash.
After breakfast, head to the Sears Tower, also on Jackson. Although I like the view from the Hancock better, going up in the world's tallest building is an experience not to be missed. (Please, no arguments about why it's no longer the tallest building...we don't care to hear it.)
Walk (or cab, if you're tired) east to the Marshall Field's on State Street. Be sure to check out the Tiffany Dome and the "Trend House" furniture exhibit.
By now you're probably ready for lunch. There are a million places to eat in the Loop. If you want to stay at Field's, their 7th floor cafeteria is pretty good. There's also the Berghoff restaurant to the south, on Adams for some the city's best German food in a gorgeous, wood paneled dining room. Bonus - it's also cheap.
After lunch, head north to Michigan Avenue. If you're into art, check out the Terra Museum of Contemporary Art (I believe it's somewhere on the 500 block). Michigan Avenue is Chicago's flashy, touristy, high-end shopping street. For a more discreet (but still high-end) experience, check out the boutiques on Oak Street at the northern end of Michigan Ave.
Wrap up your day by having a pre-dinner cocktail at the top of the John Hancock building's (also on Michigan Ave) Signature Lounge. Get a seat near a window and ogle.
Hope this was of some help! For more suggestions, check out
www.metromix.com