Ustrello wrote:Chicago-
All the museums are great and I highly suggest seeing at least one (The Shedd or MSI being my top two followed by Art Institute.
Navy Pier can be a bit tourist trappy but it is nice to see at least once
Go on the river architecture tour, you get to cruise around downtown look at cool buildings and hear the history behind them
Restaurants there are tons of them and a wide variety (honestly one of the perks living in or near chicago is the food) I have found this website to be of help when I want to find a place to eat
http://chicago.eater.com/maps/best-chicago-restaurants-38
If you can afford it go to a game at Wrigley (but with them winning this year it may be expensive or tough) and alternate is to go see the Sox as their ballpark food is out of their world and it is fairly cheap to get tickets.
There is also the skydeck in the Sears tower where you can go out 6 feet over downtown over 1300 feet
Also I would suggest the Pedway tours if you can as it takes you all over the city mostly underground and stopping off at iconic buildings.
I've been in the area for about 3 years and have done and recommend ALL of the above. For Chicago Deep Dish Pizza, go to Giordano's. Yes, I know it's a chain, but I have yet to find better deep dish pizza here.
I prefer the Chicago Art Institute to the Shed, but they're both excellent.