What do you think of this rough itinerary for this weekend in Chicago? Thanks for the previous posts by the way.
Thursday - Cubs game at 1:30. Dinner that night at either Maggiano's Little Italy or Giordano's, probably depending on what you think is a better choice for after the ballgame.
Friday - hang out by pool, Shedd Aquarium, Taste of Chicago, either Maggiano's or Giordanos, whichever we don't go to on Thursday
Saturday - hang out by pool, walk around, Navy Pier, shop, Lincoln Park zoo maybe. Dinner that night at Harry Caray's, watch fireworks at pier.

What do you think? Better suggestions? Again, from my previous posts, my wife is pregnant so we're kind of staying out of the club scene on this trip. Still welcoming other suggestions. Thanks

I think your plans sound good.
Thursday I'd probably go to Giordano's, because it's more of a casual place and probably won't be as crowded. Friday if you're going to Maggiano's I'd definitely call ahead and make a reservation. They are usually crowded on the weekends, but with a reservation you won't have to wait very long at all. It's one of my family's favorites and we've always had good service and great food. On Saturday I wouldn't go to Navy Pier til later, because the fire works aren't til after 9, maybe even ten. You could get there in time to see the sunset over the skyline, which is really beautiful.

Can I ask why you have chosen Maggiano's and Giordano's? It's just that they are both chain restaurants and don't really give you a great flavor for all that Chicago dining has to offer. There are so many great and unique restaurants in this city, and neither of those would make my list of Top 50. I'm not even talking about really expensive places (although there are plenty of those too.)

What kind of food do you like? I'm guessing Italian from your choice of Maggianos and Giordano's. Why not do Italian for one meal and then try something else. Chicago's got some great Latin/Cuban/South American restaurants (Rumba, Nacional 27, Mas, Otro Mas, Mambo Grill) and some great Asian restaurants .... these are not your typical Chinese joints .... much more creative (Red Light or Opera). There are also some fantastic French bistros (Kiki's Bistro, Brasserie Jo, Bistro Margot). And what about seafood? Try Shaw's Crab House, Bluepoint Oyster Bar, McCormick and Schmicks, Riva (on Navy Pier).

After the Cub's game, you might try Tuscany (Italian) or Otro Mas (Latin/Cuban) which are both fairly close to Wrigley.

Please let me know if you have any other questions .... I've lived in Chicago all my life and eat out a lot!

I forgot to add:

check out http://metromix.chicagotribune.com/dining/

It's a great source of reviews etc. You can do a search for any of the restaurants I listed to get more info/directions/ etc.

Thanks for both of your opinions. Much appreciated. DreamingofItaly, we aren't completely set on those restaurants and I change my mind about every 10 minutes or so. We prefer pizza, italian, steak, mexican food. One thing I left out was we are staying at Sheraton Towers at 301 E North Water St. Would you consider restaurants such as these walking distance? If so, is it safe to walk these at night. It seems that there is a lot of restaurants, shopping less than a mile away and would prefer to walk if nice outside but not sure what kind of area it is at night?? Thanks.

Couple of suggestions...
I agree with the previous poster about your restaurant choices...pretty touristy. Thursday check out some of the local restaurants by Wrigley Field, such as Mia Francessca (Italian), Platiya (Mexican), Tuscany (Italian). Good suggestion to check www.metromix.com.

Also, instead of hanging by the pool, go to the beach! Oak St or North Ave are great. Water will be cold but it is a great part of the city.

Less touristy areas to go(instead of Navy Pier) is to go to Lincoln Park, Armitage & Halstead area has some fun boutiques/stores (some good kids stores!). Have lunch at Tillis. Also Bucktown and Southport area. Ask your concierge.

Lincoln Park Zoo is a must! Have lunch or dinner at North Pond (make reservations!)

Check metromix.com for happenings around the city as well as restaurants!

Hopefully it won't be as hot as today, 90's and humid!!!!

Also, great maternity store on Webster called Swell...it's next door to two great neighborhood restaurants called John's Place and Charlie's Ale House (both have outdoor seating). A great dessert shop on the block as well.

Have a wonderful stay!

The Sheraton is great. You are fairly close (within walking distance) to Michigan Ave which is a great area. You are in the neighborhood known as Streeterville which is east of Michigan Ave. Unfortunately, there are not a ton of restaurants in that area. Both Maggiano's and Giordano's (as well as tons of other great ones) are on the other side of Michigan in the River North area. Maggiano's would be a little bit of a hike from the Sheraton (although doable ... maybe 1/2 an hour) and Giordano's would be about 15/20 minutes. I would not worry about walking at night ... the area will be pretty vibrant with people.

Anyway, if I could steer you away from Maggiano's and Giordano's (good pizza, zero atmosphere) I would like to make a few recommendations.

For Mexican: try either Frontera Grill or Chilpancingo. You could probably walk to Frontera, Chilpancingo would be a 5 minute cab ride. (It can be hard to get in to Frontera Grill so I would make reservations well in advance - before you get here). Both of these are great, unique places. They are not your typical mexican places though ... they offer a little more creative spin on your traditional mexican food.

If you really have your heart set on a Chicago-style pizza, try Pizzeria Uno or Pizzeria Due (same owners) ... you could probably walk to both. You may want to try them for lunch as they get EXTREMELY crowded at night. Many consider these two places to be the best in the city. Each is housed in a cute little house. (well, it's actually not so little)

For Italian, I would reccomend 437 Rush which is very walkable from the Sheraton.

And for steaks, Keefer's or Gibson's are great! Harry Caray's is good too (Keefer's is right across the street though, and I would prefer it.) Many consider Gibson's to be the ultimate steakhouse ... many celebrities go there, but it is quite expensive.

Anyway, all of these restaurants are relatively close to the Sheraton, you could probably walk to some of them or take a very short cab ride to others.

If any of the interest you, I would recommend looking them up on metromix to get addresses ... and see where they fall on a map. I would also try to make reservations before you get here. It is hard to get a last minute reservation on the weekends in Chicago!

Hope this helps! You'll have a great time in Chicago. Let me know if I can be of any further help.

P.S. As you are walking from the Sheraton down Illinois St. to Navy Pier, you will pass by Fox and Obel. Be sure to go in! It is this amazing gourmet food store and there is also a cafe which might be a nice place to have breakfast or lunch. (5 minute walk from the Sheraton.)

Kristy must have been typing her response just as I was ... but she beat me to the punch in posting hers. Now that I read hers, I must laugh b/c a lot of her suggestions were things I wanted to suggest too, but I figured my email was getting too long already.

I was going to suggest Mia Francesca or Platiyo nearly Wrigley too! As well as North Pond Cafe near the zoo.

I also always recommend visitors to check out the Halsted/Armitage area with a stop at Tilli's for lunch!

Anyway, now that we have sufficiently overwhelmed you ... don't worry ... there are so many great restaurants in Chicago, you really can't go wrong!

Thanks a lot for all of your suggestions. We've listened a little bit to what you've had to say and have decided against Maggianos and Giordanos. We made reservations at Wildfire, Bacchanilia on Oakley Ave which is supposed to be an excellent neighborhood Italian restaurant and also going to Pizzeria Uno. Thanks for the suggestions. Of course I'll probably change my mind again knowing me!

I would also suggest going to Mia Francesca's (my personal favorite for Italian food) and now they take reservations. I have never been to Platiyo but hear it's very good. Frontera Grill is also very good but they do not take reservations and people start lining up outside before they open. Topolobampo (the more upscale restaurant which is part of Frontera) does take reservations but it is very expensive. My favorite for pizza is Lou Malnati's. As someone else suggested I would make reservations as soon as possible for any of the places suggested unless you want to go early (6 pm) or late (9 pm).