If you are a city person then Chicago is one of the best for a short holiday.
While the Sears Tower has long queues and you have to pay, the John Hancock tower is free and has a better view.
Also well worth it is a trip on a boat around Chicago itself to see all the buildings or out onto the Great Lake for one amazing view of the skyline.
For more info check out my personal web site with a few ideas:
www.alib.co.uk/guides/index.htm
Updates
When I was there last month it was $10.25 to go up the John Hancock tower. But I agree, great views of the city. But the bar on the 95th floor is free (and has live jazz from time to time). You're both right. There is an admission charge to visit the observation deck on the 94th floor, while it is free to go up to the cocktail lounge on the 96th floor. When friends are in town I choose the latter. They usually enjoy the 70s aesthetic of the place and the views.
Go to the signature bar instead and order the cocktail of your choice and enjoy the equally good view.Expensive drinks but less than the price to go on the viewing gallery!
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