Poet Carl Sandburg once described Chicago as the “city of the big shoulders.” That phrase captures the Midwestern metropolis’ sense of swaggering possibility. This is a place where skyscrapers like the Willis Tower break records, where every neighborhood has its own flavor, where dining culture is defined by Michelin-starred temples of haute cuisine alongside heavy-duty Italian beef sandwiches and deep-dish pizza. From Chicago architecture tours to the city’s museums, from its blues and jazz communities to its theater and comedy scene, the best things to do in Chicago exist on an amplified scale.
Summer can bring soaring heat and humidity to Chicago, while winter is when the deep freeze sets in. For a less extreme experience of the Windy City, aim for shoulder season. In the spring, the Cubs return to Wrigley Field. The season is also a great time to visit the Chicago Botanic Garden or the Lincoln Park Zoo. Fall means the return of annual events like the Chicago Jazz Festival and Chicago Marathon.
Chicago is one of the Midwest’s major hubs. Two airports serve the city: O’Hare International Airport and Midway Airport. Metra trains link Chicago to the surrounding suburbs. And the city operates eight “L” rapid-transit train lines, as well as numerous bus lines. Much of Chicago is also bike- and pedestrian-friendly, and easily accessed by taxi. And don’t miss the chance to explore the Chicago River by boat.
Deep-dish pizza is a classic Chicago dish at the top of many visitors’ dining wishlists. But despite its ubiquity, this hearty style of pizza isn't the only option in town. Next time you visit, don’t forget to try the ultra-thin “tavern-style” pizza, which is cut into small square slices. It’s what the locals eat as an everyday staple.
