In some ways, Chicago, the third-largest city in the United States, does not get a fair shake as an international tourist destination. New York City, with its cosmopolitan hype, and Los Angeles, with its glitz and glamour, are preferred destinations for leisure travel to the US.

There are many theories on why Chicago is referred to as the “Windy City.” The simplest one is that its location along the shores of Lake Michigan makes it naturally breezy. The wind tunnels created by tall buildings are considered another source for its nickname. You can find other explanations here.

If you are a Torontonian visiting Chicago for the first time, you will find the cities have many similarities. Chicago sits on the banks of Lake Michigan, while Lake Ontario borders Toronto. In terms of population, the cities are similar in size and boast a vibrant cultural scene, business districts, diverse food options, and sports-crazy residents. However, as a Torontonian, I have to admit that Chicago has done a much better job of building up the city around its beautiful lakes and promoting it to visitors.

The first thing that strikes you about Chicago is that it has a lot of skyscrapers. Each one has its own unique architecture. With creative architects leveraging innovative structural engineering techniques, Chicago’s architectural scene has evolved as a significant draw that brings domestic and international visitors to the city.

Chicago is a big city with a vibrant downtown core and is home to world-class museums, cultural venues, and an upscale shopping district. Many outdoor venues, such as the Navy Pier, are great for catching a cultural event or concert, often available at no cost to the public.

From upscale shopping on the Magnificent Mile to sampling deep-dish pizza to taking in performances at a blues bar, Chicago offers a variety of options to engage and entertain tourists to the city. Chicago’s food scene is second to none, with budget options, hot dog outlets, and fine dining establishments.  

Home to legendary teams such as the Bulls, Bears, and White Sox, the city is prime for sports tourism.

Chicago can get cold and snow-laden during the winter months. If you want to take advantage of its beautiful river walks and beaches, you should plan to visit the city between the spring and the fall.