Southwest® flights from San Francisco to Chicago (O'Hare) from $100

Towering over Lake Michigan, Chicago combines big-city energy with Midwestern hospitality. A day there really is whatever you choose to make of it. Millennium Park has plenty of attractions to explore. Take in a symphony at the unique Jay Pritzker Pavilion bandshell. Grab a selfie at Crown Fountain, a video sculpture and interactive piece of art. While your camera is out, be sure to head over to the Cloud Gate. Affectionally called “The Bean” due to its shape, this sculpture's shiny surface reflects and alters the view of the surrounding skyline. And you can walk under its 12-foot-high arch. If you have a hankering for ballet, modern dance, or opera, head to the Harris Theater for Music and Dance, which is also located on the grounds of this stunning downtown park.

Chicago is home to some of the most beautiful architecture in the country. A good example is the historic Water Tower, located along a stretch of Michigan Avenue aptly known as the Magnificent Mile. A former water pump building that withstood the Great Chicago Fire, it’s now home to the City Gallery, which features the works of local filmmakers, artists, and photographers. As you stroll down Michigan Avenue, famous for its shopping and busy sidewalks, you also take in other Chicago landmarks and architectural marvels like the Tribune Tower, Michigan Avenue Bridge and Esplanade, and the John Hancock Center.