There are many ways to get to know a city, but few are better than the plethora of Chicago tours that explore the Windy City’s storied past and rich culture. The Chicago Architecture Foundation, for one, leads wanderers on treks that highlight the city’s classic buildings and the modern skyscrapers that compose its world-famous skyline. Beneath downtown Chicago, visitors can learn about the city’s history while shuffling along the Pedway, an underground labyrinth of connected walkways. And for those looking for an even more unorthodox introduction to Chicago, there are sightseeing tours that detail the town’s seedy crime history, others that take groups kayaking along the Chicago River, and even some dedicated to the city’s signature deep-dish pizza.

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