The Chicago CityPass is really an excellent value if you're planning on visiting all the attractions it offers. At the time of purchasing, the CityPass was $49.50. You can purchase the CityPass at any of the CityPass attractions, but I would recommend the Hancock Tower, since the lines there are usually shorter. After purchasing the CityPass, you are often able to go into a "Will Call" line at the other attractions. This saves time, since you don't need to wait in the general admission lines.
The city pass is valid for 9 days. We went through all the attractions in 4 days. The time to go through each attraction is listed in the individual reviews.
The Chicago CityPass includes the following attractions (click the link to read the review for that attraction):
The Chicago CityPass was $49.50 at the time of writing.
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John Hancock Tower - Observatory
Adler Planetarium
The Field Museum
Shedd Aquarium
Museum of Science and Industry