Take an architecture/history boat tour. Also, depending on the ages of your kids, you should take them to the science and industry museum (younger kids will like more than 14+ year olds).
Go get some deep dish pizza from giordano's. navy Pier is a waste of time.
I second going to the Science and Industry Museum - it was my favorite when I was a kid. Depending on your kids, they might like the miniature rooms at the Art Institute. Millennium park is nearby as well, and a must see if the weather is nice.
Also, have a proper Chicago style hot dog and an Italian beef. I like mine juicy with hot peppers.
I'm also headed to Chicago on the 23rd and would love any recommendations on where to eat and what to do. We're headed to the Cubs game on Friday against Cincinnati. Other than that the schedule is open. Thanks in advance.
As others have said the MS&I is a must see, but look online ahead and plan what you want to see there. Some of the exhibits like the Coal Mine and the German Sub get quite crowded. And the museum is HUGE! So plan your trip. Museum of Science & Industry Also - MS&I is on the south side, near Univ of Chicago, an all day trip.
Field Museum, Adler Planetarium, and Shedd Aquarium are all close together on the lakefront, so it is easy to do bits and pieces of each of those. Field Museum Field Museum is my favorite, but Art Institute is also worth a stop. During the summer, the symphony often practices in the Grant Park bandshell. Nice to grab a sandwich and sit, eat lunch, and listen for free to some beautiful music.
Pizzeria Uno and Due have always been a favorite of mine. Not the stuffed crust pizza, but great thick crust. They are about a block apart at Wabash and Ontario and Wabash and Ohio. Giordano's is what you want if you are looking for stuffed crust.
Wendella Boat tours of the river and the lake have been operating since my parents were kids, and they are a nice little relaxing way to see some of the architecture and the city, especially if you have kids. We did a tour almost every summer and never got tired of it. Wendella Boat Tours
Wrigley Field is a no brainer, go early, stay late and take in all that is Wrigleyville. Make sure the hot dogs are Vienna dogs with poppy seed buns. An Italian Beef sandwich wet with peppers is also on the "gastronomical" must list. Portillo's is good for these, but people usually have their neighborhood favorites too. Portillo's is found in lotsa locations including downtown.
If you are an architecture fan, head out to Oak Park for a Frank Lloyd Wright Tour Shop the Mag Mile and take a look at Water Tower Place. Learn a little about the structures that survived the Great Fire. Brownstone Tavern on Lincoln Ave is the TexasExes headquarters during games.
Have fun! It is a great place to visit. You can't be bored!
Also, you should do the tourist thing and go up the Sears Tower...they have a new feature somewhere above the 100th floor where you walk out into a glass box and look down at the sights below.
Lived in Chicago for 3 years during grad school.. I lived up "north" though.. like north burbs for school. I would welcome any private messages for particular questions for food. etc.
Wendella boat tour is a MUST.
Also, I don't think anyone mentioned it yet, but try the 'lounge' in the Hancock tower over Sears Tower. It is free to get up there, it is a bit lower.. I think 98th floor, where Sears is 103rd... something like that.. but the positioning of the tower is better to look out over the lake and see more of downtown, and again it is FREE.. you do have to buy an expensive drink, but hey, that is just more of the fun!
Lou Malnati's is great! The best pizza in the area in my opinion is either at My 'Pi's" the symbol 'pi' really, or buffo's up in highwood.
Also check outThe Link if you want a GREAT meal. It is the top rated Italian restaurant in the midwest, and the experience is amazing as well as the food. Anyway, I have other idea, if you have specific questions.
I am really needing to take my wife there. as she has NEVER been there, and it is like my second home
Puffer, thanks for the reminder! LP Zoo is great! On the lakefront, nice atmosphere, and animals that are more active than any zoo I have been to. Lincoln Park Zoo
if you go to the LP Zoo, be careful around their elephants. They are notorious for throwing their poo at visitors. This might sound like a joke, but I promise you this is no joke.
Buffo's and My Pi's should be on that list. Gino's east was NEVER my favourite. Too much corn in the crust and too heavy on the crust... Buffo's doubledecker pizza is WOW.
I still say eat the best meal of your life at Gabriel's in Highwood.