Experience Chicago from every angle on this immersive small group tour that blends the city’s world famous prohibition architecture with its most iconic flavours. Over five hours, you’ll explore soaring skyscrapers, historic landmarks, hidden interior spaces, and the city’s unique underground Pedway, offering a perspective most visitors never see.

Your expert local guide shares the stories behind Chicago’s architectural evolution, from the post Fire rebuilding to the rise of modern design. Wander through The Loop, admire beautifully preserved Art Deco details, and step inside remarkable interiors that reveal the city’s creative spirit. Along the way, enjoy a seamless balance of outdoor exploration and behind the scenes access.

Between architectural highlights, you’ll savour a delicious lineup of classic Chicago eats. Enjoy a hot, cheese laden deep dish pizza slice, a Chicago style hot dog, juicy Italian beef, and buttery local popcorn, tastings that together create a satisfying meal and a flavourful journey through the city’s culinary traditions.

With a maximum of 12 guests, this tour feels personal, relaxed, and interactive, offering plenty of time for questions and stories. As a Certified B Corp and carbon neutral operator, we’re committed to running experiences that positively impact the community.

Perfect for architecture lovers, food enthusiasts, and first time visitors alike, this tour reveals the real Chicago, its skyline, its flavours, its hidden pathways, and the vibrant history that ties it all together.