Top Chicago Luxury Tours

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested...

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends,...

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to...

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean",...

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer...

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold...

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...

Recently voted one of Cool Shore Excursions's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut...

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s...

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic...

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum...

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the...

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views...

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s...

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high...

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to...

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local...

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings....