The tourists always seem to be having fun, I just get bored.
Navy Pier is a fun destination for families. It has the Chicago Children's Museum, a hands-on facility for kids to play in, a lot of restaurants, an imax theater, a ferris wheel an carousel in the summer and fall, ice skating in the winter.
Many harbor tour boats launch from here. Other than that it is easy to get consumed in the over-ratedness of this locale.
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At Least Do This: Ride the Ferris wheel.
If you have kids go to the Children's museum
See the crystal gardens
Go for fireworks in the summer. Wed and Sat nights at 9, (arrive around 8:30)
Alternative: I mean it is something to be seen in the city so you should at least check it out if you want to.
Museum of Science and Industry (57th and Lake Shore Drive)
Millenium Park (Monroe and Michigan Avenue)
Lincoln Park Zoo - Fullerton Parkway and Cannon Drive
Peggy Notebart Museum - Lincoln Park, Chicago