Top Chicago Luxury Tours

Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike...
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Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a...
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Come aboard the Odyssey Chicago River for a delicious, freshly prepared meal while taking in the best views of Chicago's infamous architecture. Sit back, relax,...
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Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some...
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Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or...
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Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that...
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Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or...
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Let us put the Custom in Chicago Custom tours… What are your must-see venues? What would personalize your excursion? We’ll plan your tour and make...
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Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night. Enjoy breathtaking views of the dramatic skyscrapers...
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See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night. View Buckingham...
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This experience is as unique as it gets, as you will be allowed to take to the controls and see just what it takes to...
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See Chi-Town in a brand new light by night on this City Lights Segway Tour. There’s nothing quite like spending a summer evening along the ...
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Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This tour takes you to some of the city’s...
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Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown...
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Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun...
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Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern...
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Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on...
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Experience the best travel stories for yourself! Join a local expert and uncover hidden gems on this Lonely Planet Experience powered by Urban Adventures.Join us...
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Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a segway at night. Venture through the dark...
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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....
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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...
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