A Different Way To Experience Chicago

With so many sky-high sights and so much to do, it can be hard to get a handle on Chicago. These handpicked tours and experiences take you away from the crowds and give you a fresh, hands-on take of Chicago.

Chicago has certain must-dos on every visitor’s checklist: try deep dish, visit Chinatown, learn the history and give a hearty “Oooh!” at the designer skyscrapers. But ticking those off away from teeming crowds and with local, experienced guides is one of the most fun ways to get a fresh look at the city. Don’t just eat deep dish – make one! Why settle for just history or just architecture when your tour can have both – plus bites! Discover secrets and go behind the velvet curtain (sometimes literally, at the Chicago Theatre) to get truly unforgettable insights into the real Chicago.

Tours

Enjoy Chicago’s only bus-guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

Tours

Join this 3-hour tour of Chicago’s food scene, and see what sets this friendly Midwestern metropolis apart. On this 12-person-maximum walking tour of the ‘Chicago Loop’, a local guide will share with you some hidden gems and great stories about the city. Taste where the world-famous dipped Italian beef sandwich was invented, try some of the best deep dish Chicago pizza. Be shown how important the immigrants that built this town are to the food scene.

landscape with balloons floating in the air

KEEN TO EXPLORE THE WORLD?

Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.