To help you craft the perfect, self-guided journey through Chicago in 2027, we have scoured the city’s vibrant neighborhoods to curate a list of standout restaurants and bars.  These are the hidden gems and local favorites where Chicagoans actually eat, each boasting spectacular reviews, unique ambiance, and food that tells a story.

A self-guided audio tour is the ultimate travel hack for the Chicago Loop. It delivers the deep, immersive storytelling and historical context of a premium guided tour, but it hands the control entirely back to you. It is the absolute best way to see the city on your own terms. Here is why downloading a tour to your phone will completely change the way you explore Chicago.

Few urban centers capture the spirit of ambition, resilience, and creative reinvention quite like downtown Chicago. Every street corner tells a story of visionary architects, pioneering engineers, and bold civic leaders who transformed a swampy frontier trading post into a towering metropolis of steel and glass.

The real magic of Chicago lies hidden in plain sight. It is tucked away in its diverse neighborhoods, concealed within historical underground corridors, and blooming in quiet architectural marvels that most tourists completely miss. If you want to experience the Windy City like a true local, you need to step off the beaten path and look beyond the glossy tourist brochures.

Discover some of Chicago’s most distinctive dining and drinking spots with Drives & Detours. These local favorites are beloved for their unique flavors, standout ambiance, and cultural significance

Explore the best things to do in Chicago with Drives & Detours’ guide to the city’s top attractions

Heading to Chicago? From unpredictable weather to the best neighborhoods, here’s Drives & Detours’ guide to exploring the Windy City like a local