Chicago

Experience the bold heartbeat of Chicago, the Windy City, where the soaring Willis Tower (formerly Sears) offers vertigo-inducing Skydeck views from glass-bottomed ledges, the iconic Cloud Gate (“The Bean”) reflects a skyline of architectural masterpieces along the Chicago River, and the dramatic Navy Pier stretches into Lake Michigan with Ferris wheel spins and fireworks over the water.

Stroll the Magnificent Mile’s luxury shopping and Millennium Park’s free concerts, cruise the river on architecture tours past Frank Lloyd Wright influences and modern skyscrapers, explore world-class museums like the Art Institute with its iconic American Gothic, or savor deep-dish pizza, Chicago-style hot dogs, and craft beers in vibrant neighborhoods from Wicker Park to Chinatown—all in a city blending Midwestern warmth with big-city ambition and 26 miles of stunning lakefront trails.

Indulge in juicy Italian beef sandwiches, buttery Garrett’s popcorn, and rooftop cocktails amid legendary sports passion, summer festivals, and resilient spirit that turns every visit into an unforgettable urban adventure.