Chicago, IL
An iconic city of architecture, art, and brutally cold winters
Chicago is a city that blends bold architecture, rich history, and a vibrant creative spirit along the shores of Lake Michigan. From the soaring skyline and world-class museums to riverfront walks and legendary deep-dish pizza, every neighborhood tells its own story. The Loop anchors it all, where culture, commerce, and design meet in a dynamic downtown core. Explore the city’s landmarks and hidden gems at your own pace with our self-guided walking tours.
Self-Guided Tours in Chicago
Chicago Loop Self-Guided Audio Walking Tour
The Loop is the vibrant center of Chicago where soaring architecture, legendary art, and centuries of history come together. From the Willis Tower and the Art Institute to Cloud Gate and the Chicago River, every block tells a story of ambition and reinvention. Explore the city’s architectural icons, public plazas, and hidden corners with GPS-activated audio on this self-guided walking tour.
Top Sights & Attractions
Top Sights & Attractions in Chicago: 5 Must-See Highlights
Few cities blend architectural brilliance, artistic innovation, and Midwestern charm quite like Chicago. The Windy City offers a skyline that inspires awe, food that feeds the soul, and lakefront views that seem endless, whether it’s your first visit or your fifth. No trip is complete without checking off a few of the city’s most iconic landmarks. These are our five can’t-miss experiences.
Favorite Food & Restaurants
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Tips & Travel Information
Chicago Travel Tips: Insider Advice for First-Time Visitors
Chicago, known as the Windy City, is one of America’s most dynamic urban destinations. Its soaring skyline, rich history, and vibrant neighborhoods make it a must-visit city. Drives & Detours' practical insights will help you get the most out of your trip, whether you’re here for a weekend or a longer stay.