My town is too small, LOL with not much to do other than shop at local chain stores.
The
ONE must see in Chicago? Thats impossible. Heres a list of options.
**cracks knuckles, inhales sharply**
BEAR WITH ME HERE! LOL I cant just name
ONE!
Sears Tower: Standing 1,353ft above the street and being able to see MI, IN, IL and WI. Too cool.
John Hancock: Great observatory deck, 3rd tallest building in the USA, best views of downtown. Outdoor observatory HAS to be experienced, particularly at night.
Michigan Avenue: One of the best shopping streets in the world, hands down. So much to do and see (Oak St. offers the super high-end shops)!
The Lakefront: Take a boat skyline tour on one of the many charter boats, the speedboats are particularly cool.
Adler Planetarium: Great place to take the kids, lots of neat interactions and hands-on activities.
Navy Pier: Super cool place to shop or hang out. A huge ferris wheel, some other rides, indoor dining, games, boat rides, you name it. Super cool place!
Museum of Science and Industry: Another great family place. Tour a coal mine, walk on the U-505 (captured German U-boat), walk inside a human body, mess around with electricity, etc... WAY COOL.
Theatres/opera: Catch the Chicago Symphony Orchestra, a popular play, Blue Man Group, etc... here in Chicago as well. If that stuff bores you, there is always Oprah and Jerry Springer! LOL
Field Museum of Natural History: See the man-eating lions of Africa (the movie Ghost and the Darkness is based on these lions), see Titanic artifacts, tour an ancient Egyptian tomb. Another super cool place to take the kids.
Chicago Art Institute: Besides the Louvre, probably the best art museum in the world. Priceless works of art all encased in a gorgeous building.
Water Tower Place: A huge vertical indoor mall, chock full of shops and eateries.
Water Tower: One of the few buildings that survived the Great Chicago Fire, stands at the far north end of Michigan Avenue.
Oak St. Beach: in the summer its a great place to relax and hang out. Gets crowded too fast, so get there early and set up shop. Swim, rollerblade, beach volleyball, etc.
Millenium Park: rather new, but cool to see regardless. Neat sculptures (Cloud Gate is really cool), water fountains, music venue, historic Roman columns, neatly sculpted landscape, ice skating rink in winter, restaurant.
Buckingham Fountain: arguably the USA's prettiest fountain. Its HUGE and needs to be seen in person to appreciate its size. Looks gorgeous at night. Shes a lady in a black dress and pearls, no doubt.
Shedd Aquarium: right on Lake Michigan, its a huge aquarium with TONS of super exotic fish, and a brand new addition for whales and sharks. Great place for families and the like.
Sports: catch a Sox game at U.S. Cellular Field on the south side, a Cubs game at Wrigley Field on the North Side, a Bulls or Blackhawks game at United Center on the near west side, a Bears game at Soldier Field along the lakefront. Then there is the Chicago Wolves at All-State Arena, or the Kane County Cougars at Elfstrom Stadium, and the Schaumburg Flyers in Schaumburg, the last 3 mentioned teams are in the 'burbs though.
Dining: not much to say. You all know how good the food is here, and there is 10K restaurants in teh downtown area alone (from what I understand), so the options are endless. You want good food, come to Chicago.
I could go on, and on, and on, and on... but my brain is fried. If I think of anything else later, Ill add to this list. Sorry so long!
**ADDED**
Lincoln Park Zoo: Hang out in the park, see the great zoo, take a paddleboat out on the lake they have. Another nice place for the kids to hang out at.
Wendella Boat Tours: take a architectural tour of the city right from the Chicago River. Not expensive and a really tireless way to view Chicago's world renowned architecture.