If you're talking food, something like Italian Village, Gene & Georgetti's (probably got the names wrong, but the phonietics are right), Trader Vic's @ the Palmer House, Chicago Pizza & Oven Grinder (*very small place*, plan on waiting), Morton's is OK, expensive, and no real thrills ...The 95th (restaraunt at the top of the Hancock Tower).
Out in the 'burbs - Wheeling - Tuscanay, Cafe Lucci (*the Best* High falootin' I-talian in the city), The Blackhawk (aka Don Roth's), Pete Miller's (original Pete's is in Evanston .. killer red meat - steaks bigger than your head), Bob Chin's (also not nevessarily romantic, but excellent seafood by any standard).
Pizza - Thin Crust: Gino's, Pizzaria Uno, Pan / Stuffed: Nancy's, Pan - Lou Malnatti's (the sausage pizza has a single slice of sausage - if you get a 14" pizza, it will have a 14" wheel of sausage covering the top)
There are (may be - check with the concierge desk) some Dinner cruises leaving from North Pier - if the lake is frozen, they tend to stay in the breakwater.
Navy Pier has some places.
The Shedd Aquarium is nice, the Art Museum is nice, Water Tower Place, Druary Lane theater, The Blue Man group is still playing, "Wicked" - Oz before Dorothy dropped in, is playing, there might be something up at the Opera, Chicago Symphony might be playing ...
See if your local library (or book store) has the Friday additon of the Chicago Trib: that usually has "everything" that's going on in Chicago for the next couple weeks.
Good Luck
Scott
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