Chicago makes such a striking impression that you're best off discovering it from a few different vantage points. Luckily, Chicago tours offer multiple ways to see the city in style. Visit the observation decks in the Windy City's record-breaking skyscrapers for panoramic views; then, hop on a boat along the Chicago River. From there, zoom into a more local scale: Head out after dark to learn about the city's gangster history; explore its characterful neighborhoods on local-led walking tours—and don't forget to eat Chicago classics, from deep-dish pizza to Italian beef sandwiches, on a tasting tour.