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whenever i go back to chicago, where i grew up, i only ever have to eat at two restaurants: walker brother's pancakes in wilmette, and pizzeria due, which is at 619 wabash, just a couple of blocks from where you'll be staying. it's idiosyncratic deep dish chicago pizza and i dream about it, especially the sausage.

you'll be sort of close to the art institute, so if you're an art museum person, i highly recommend it, since it has a world class collection {including very famous paintings by grant wood and georges seurat}.
other wonderful museums are the field museum of natural history, and the museum of science and industry. and the museum of contemporary art, which has rotating exhibitions.

there's also {well, there were, anyway, when i grew up in the 70's} a wonderful acoustic music scene, and some splendid theater -- steppenwolf, second city and goodman are the three most famous, but there are lots of little theater companies.

if you like shopping, you'll be close to a lot of high end stores on michigan avenue, especially around state street.

there's also the beach, if you are so inclined. there are sand beaches in rogers park that i used to love as a child.

if you enjoy baseball and don't mind seeing the home team lose, wrigley field is a little jewel of a ball park.

My favorite tapas restaurant in Chicago is Cafe Iberico... I can't remember the exact address, but it's on an avenue parallel to Michigan (I think it's Ontario). Great ambiance and great food. I always go eat there when I am in the city.

And I also love the walker brother's idea, but it's far from the downtown area. I used to go to school in Evanston and it's farther north on Sheridan Road. The L doesn't get there and it's about a 45 min drive from downtown.

Now thinking about it... if you're into Top Chef, why not seek out the winner of last season's, Stephanie, restaurant???? I bet it's super good eats...

Cafe Iberico is on the east side of LaSalle about a block south of Chicago Ave.

Bandera is a great restaurant just south of Ohio a few blocks on Michigan. It's on the second floor above Andriana Furs, on the east side of the street. Comfort foods with a sophisticated twist. Very affordable. Live jazz every night, seats at the window overlook Michigan Avenue. It's my favorite spot in Chicago. Then go across the street and up a block to Grand Luxe Cafe for a monster dessert.

To pass the time on your free day, take a free trolley around the city. Go to visitors center at Water Tower (north on Michigan Ave to Chicago Ave) and get a map of the trolley routes. Get off wherever you like (Shedd Aquarium, Planetarium, Sears Tower, Art Institute, etc.) and hop back on. Just pay attention to the time of the last trolley so you're not stranded. Even so you could catch a cab. I recommend the Art Institute-- even though many of their paintings are on vacation in Texas, there's still a lot to see. Also, get drinks in the Signature Room on the 96th floor of the Hancock. The best view is actually from the ladies restroom up there.

If you're interested in architecture, google the Chicago Architecture Foundation-- they have walks and boat rides which are lovely and interesting. Also google the mayor's office of Chicago to find out what festivals are going to be going on while you're there. There's often music or movies playing in Grant Park or Millenium Park, a nice evening activity. Enjoy!

If you don't mind seeing the home team lose? Ouch. The Cubs are rocking the standings this year. And any day at Wrigley is a hell of an experience. Plus those greasy dive burritoes right next door are the things dreams are made of.

I 2nd the Bandera comment, it's a very good restaurant on Michigan Ave near Ohio. Most of the restaurants in that area are very touristy so be careful. You've got to hit one of Chicago's steak houses. My favorite is Gibson's which is maybe 1 miles north of where you will be staying ... a closer option is the Chop House, a very old school chicago steak house (bring your wallet). You should also definitely have a cocktail at the signature room on the 95th floor of the John Hancock building. Why pay to go to the sky deck when you just need to buy a drink at the bar and have all the views you need? If you're into sushi, try South Coast on South Michigan Ave (a cab ride will be needed and it's BYO).

I had a great meal at Coco Pazzo Cafe which is at 676 North St. Clair. It's not nearly as big as the original Coco Pazzo, but it's cozy, bustling and very nice. I don't know if the link will show up here, but I'm pasting it below.

http://www.cocopazzocafe.com/

If you're looking for a nicer meal, I highly recommend Naha, it's on Clark and I believe Illinois, right up the street from Bayless' places. Also, if you want to take a bit of a cab ride, May Street Market on Grand and May is amazing, and they have a $32 pre-theater three-course prix fixe this summer that goes up to 8 pm. I haven't been, but I hear amazing things about Kiki's Bistro on Franklin, which is a few blocks of a walk, but the weather's nice. Though I wouldn't eat there for dinner, the brunch at Tavern on Rush is pretty nice and affordable, and there's a lot of outside seating for people watching on the triangle. I'd also second the Lula Cafe recommendation if you find yourself up in Logan Square for any reason I would definitely check it out.

I second the previous suggestions of Bin 36 and Cafe Iberico.

Also try The Gage, a gastropub on Michigan Ave. across from Millennium Park. Good beer selection, interesting pub food-type appetizers, and plenty of larger plates for lunch or dinner.

For coffee downtown, definitely hit up Intelligentsia Coffee on Wabash and Randolph (just one block west of Michigan Ave)--try the cold-brewed iced coffee. Many buses run up and down Michigan Avenue, so you'll have no trouble exploring from your hotel.

I recently spent a weekend eating all over downtown Chicago. Cafe Iberico is certainly not the best tapas around (depends where you're from I guess) but it's definitely the cheapest. Heaven on Seven is near you--I didn't make it there, but people recommended it for a Cajun breakfast.
If you want to try stuffed crust pizza, there's a Giordano's near you. But definitely go with a group so you can get a regular size pizza instead of the individual.
I second the Intelligentsia rec if you like coffee, it's really really good.

For touristy stuff, I recommend the architectural boat tour and definitely google Chicago SummerDance, they're free outdoor concerts in various locations throughout the summer, with free dance lessons (salsa, swing). You'll want to do some dancing after eating all that yummy food. Also Navy Pier has fireworks twice a week.

Just a note that the Garrett's on Michigan Ave. has closed.

Bandera and Grand Lux Cafe are solid, but they're chains. I'd suggest you focus on restaurants that you won't find anywhere else in the world.

If you like Thai food, consider jumping on the Red Line to Sheridan and check out Spoon Thai...if your only exposure to Thai food has been at restaurants in the US, you'll be in for a treat. (Make sure to ask for the translated menu, which includes some gems.)

Chicago has some of the best authentic, regional Mexican food in the US, thanks in part to our large Mexican-American population, and the influence of Rick Bayless, who runs Frontera Grill and Topolobampo. Many chefs who have trained under Bayless have gone on to open great places themselves. Among the ones to consider are Mixteco Grill (http://www.lthforum.com/bb/viewtopic.php?f=14&t=19245) at 1601 W. Montrose Ave. (a cab or L ride away) and Sol de Mexico (http://www.lthforum.com/bb/viewtopic.php?t=9213) at 3018 N. Cicero (also a cab ride or L ride away). If you're looking for a Mexican place that's a bit more low-key and closer to Michigan Ave., get a gordita at Perez Restaurant at 853 W Randolph St.

Chinatown also has some standouts, and is easy to reach on the L. Phoenix (http://www.chicagoreader.com/cgi-bin/rrr/details.cgi?numb=666) is a favorite for dimsum. It's located at 2131 S. Archer Ave. Many people swear by "Little" Three Happiness (not to be confused with the bigger Three Happiness located across the street), which is a Cantonese restaurant. Dish suggestions can be found at http://www.lthforum.com/bb/viewtopic.php?t=3716 and the restaurant's located at 209 W Cermak Rd.

I'd also suggest you review the "Great Neighborhood Restaurants" awards here http://www.lthforum.com/bb/viewtopic.php?f=28&t=15149 as well as the recommendations of Check Please (http://www.checkplease.tv/) reviewers.

GAH! I love Streeterville food. And there is a lot to do. Definitely worth a walk to the end of the pier just to look out over the Lake. I miss it so much! And drop in the Billly Goat at the Pier and try and order fries.

My fav place to visit when I do is Copperblue. Lil pricey, but YUM.

Also digging Niu Japanese Fusion.

Dick's last Resort is always crazy loud fun at night.

Make sure you get a Chicago Daaag dragged through the garden while your there.

So jealous...