Chicago Experiences

Tour Chicago with a Local Expert Guide

Popular Chicago Experiences

Chicago is a lively city bursting with distinguished architecture, diverse neighborhoods, and a rich culture of food, history, and music throughout.

Filled with friendly folks from all walks of life, Chicago is a welcoming place to explore and you’ll see why millions of people happily call this Midwest metropolis home.

Private Step-On

Step on Guide Service Chicago

Embark on an exciting exploration of Chicago with our Step-On tour services. Our local expert guide will join you on your Chicago experience!
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Driving Tour

Chicago City Private Driving Tour

Join us as we cover the absolutely iconic sites of Chicago! Take some photos at Millennium Park, view the soaring skyline of The Loop, see the city’s most iconic sites on The Chicago Riverwalk, and so much more in this custom experience!
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Walking Tour

Chicago TV & Movie Locations Walking Tour

A tour designed to hit some of Chicago’s must-see TV & movie filming locations may include stops at locations from hit movies like The Dark Night, My Best Friend’s Wedding, and Ferris Bueller’s Day Off!
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Community Impact

By limiting tour group sizes, WeVenture promotes togetherness and accessibility and gives us the chance to build stronger relationships with our guests and connect them to Chicago. Whether you’re with family and friends or flying solo, we’re able to share impactful experiences that create strong memories and bring people closer together in our community.

Our food tours help support Chicago’s vibrant culinary scene. While our guests enjoy the best of the city’s fine dining and street food on our tours, our local vendors benefit from the unique relationships we build with them over time.

Our tours aim to increase awareness of Chicago’s public thriving arts and culture scene, featuring both internationally recognizable and local artists that in turn help inspire our guests and support the arts.

Choosing a tour experience that includes walking and public transit helps us reduce our carbon footprint and contribute to a more sustainable city.

What Our Customers Say

In December 2024, our group of 11 senior pax had a whale of a time in Miami.

 

We crafted the itinerary with Michiel of WeVenture Travel. It has every experience that every visitor would like to have. From limo travel to power boats, Bay Cruise and party over a cabaret show.

 

Chip, the guide, delivered the itinerary with patience and passion. We had plenty of Miami travel tales to tell over coffee and tea. Thanks to Michiel and Chip of WeVenture Travel.

Highly recommend travelling with WeVenture Travel!
Wen Ko - December 2024

Highly recommend Kristina as a tour guide in Colorado. We had such an amazing experience with her as a local. She was well-prepared and very organized throughout the whole trip making last-minute adjustments ensuring the best experience for us. She was very considerate of our interests and tailored the trip to our liking.

Kristina has deep historical knowledge of Colorado and provided so many insights on not only architectural sights but also on local landscapes.

Highly recommend Kristina as your tour guide through Colorado, it is going to be an unforgettable trip for you and your family.

Excellent introduction to Colorado!
Mila Romanova - October 2024

My family of 6 took a 1.5-day customized tour with WeVenture Travel, covering Las Vegas, Zion, Page, and the Grand Canyon. Michiel was quick to respond, creating a personalized itinerary and webpage. Our guide, Jim, was fantastic—engaging, accommodating, and always putting us first. The whole experience was seamless, making it a stress-free trip for first-time US visitors. Michiel and Jim exceeded our expectations, and I highly recommend WeVenture Travel.

5/5 stars—thank you for the unforgettable memories!

Short Break visit to Zion National Park, Grand Canyon National Park and Page, AZ
Charmaine See - December 2024

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