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I love restaurants, so I hope I can help you out by offering a few suggestions.
In the downtown area, there are many good ones...so you have tons and tons of options. If you're in the mood for Italian, I like Trattoria No. 10, at 10 N. Dearborn. The Atwood Cafe, at 1 W. Washington, is good for comfort food, but is also good for dessert and drinks later in the evening; it is a VERY cute place. I've heard very good things about Russian Tea Time at 77 E. Adams, but I've never been there. One of the new hot spots (although I haven't been there, either) is Sugar at 108 W. Kinzie. They serve only dessert and drinks.
If you're looking for a good place to get a quick lunch, Zoom Kitchen is awesome and they have some of the best salad, ever. There's on at 923 N. Rush, and there's also one downtown at State & Jackson.
One of my FAVORITE restaurants of all time is Tizi Melloul, at 531 N. Wells. It's Mediterranean and the food is amazing and the decor incredible and sexy (yes, I think decor can be sexy). It is a beautiful restaurant with inventive food that isn't too, too expensive, the people are friendly and the drinks great. It's really a great experience.
If you want to venture out of the downtown area (and I recommend that you do because that's where you can find true Chicago character) there are more great places. In the Old Town neighborhood, you can get great Mexican food at Adobo Grill, at 1610 N. Wells. The guacamole is to die for and they make it with fresh avocados right at your table. In the Wicker Park/Bucktown area (which is northwest of downtown) there are some good places as well. Mod, at 1520 N. Damen, is a fun place to see and be seen and the food is good as well (although it's not a good place for vegetarians). Nearby D'Vine, at 1950 W. North is fun as well, and they usually have good music and they have a great wine selection. If you want funky and unique, check out Privata Cafe at 1938 W. Chicago. They describe their food as Italian with a touch of Mexican, and the pasta (especially the pasta with black bean chipotle pesto) is wonderful and it's cheap and BYOB so you can grab wine at the liquor store on the corner. This is another of my favorites. If you want to get brunch, Wishbone at 1001 W. Washington is the best place to go. The food is southern (great black bean cakes and corn muffins) but you'll have to wait a while to get a table.
Of course you should not miss Chicago pizza, and IMHO the BEST place to have it is at Pizzeria Uno (29 E. Ohio) or Pizzeria Due (619 N. Wabash). They're both run by the same people, but I personally always go to Due. The pizza is the best pizza I have ever had in my life and worth the crowds and the wait. Keep in mind that if you're going to go to Uno, ONLY go to the original one! There are chains all over the place now, but the pizza at the other Uno locations is not NEARLY as good -- not even close.
Ditto what Kate said about Field's -- no visit to Chicago would be complete without checking out Marshall Field's on State Street. You could LIVE there; they have everything. If you want to eat there, I think that the food court on the 7th floor is better than the one in the basement.
If you want to go out for a nice evening of jazz, you should check out the Green Mill. It's way up on the north side at Lawrence & Broadway, but it's worth the trip. It's an old school place (where Al Capone used to hang) with incredible live jazz and mellow, decent crowds.
I'm pretty sure the Sears Tower is open. I was working a few blocks from it right after 9/11, and they reopened it way back then, so I'm sure they're probably open now. If you don't want to go there, you can always go up to the bar atop the Hancock center and have a drink -- great views, but you don't pay admission to the skydeck (just the price of a drink).
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