For the skinny on Chicago's skyline, look no further than the Chicago Architecture Foundation (CAF).
The foundation operates numerous tours -- walking, boat and bus -- that educate participants on more than 60 architectural sites in and around Chicago. Of the CAF's many options, travelers most recommend the Architecture River Cruise, which meanders along both the north and south branches of the Chicago River.
This tour gives you a really great overview of the city and its history, worth every penny.
The Chicago Architecture Foundation offers tours throughout the year, although they are not as frequent during the winter. Prices vary depending on the type of tour you wish to take.
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