Luxury Tours in Chicago
Top 10 Best Chicago Luxury Tours
Found 31 Luxury Tours activities in Chicago. Sort by Popularity.Chicago by Night: 90 Minute River and Lakefront Cruise
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 and Buckingham Fountain's spectacular light display. Hear lively commentary as... More
![Chicago by Night: 90 Minute River and Lakefront Cruise Chicago by Night: 90 Minute River and Lakefront Cruise](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/38/d1/5f.jpg)
Chicago by Night: 90 Minute River and Lakefront Cruise
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Chicago
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Exellent111 reviews4.2
Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! E....
Chicago in a Day: Food, History and Architecture Walking Tour
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 of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago d... More
![Chicago in a Day: Food, History and Architecture Walking Tour Chicago in a Day: Food, History and Architecture Walking Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/8c/70/1a.jpg)
Chicago in a Day: Food, History and Architecture Walking Tour
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Chicago
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Superb847 reviews4.9
Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epi....
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which... More
![Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/36/9c/ba.jpg)
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
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Chicago
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Superb586 reviews4.9
Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour g....
Chicago City Tour with Architecture River Cruise Option
Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned ... More
![Chicago City Tour with Architecture River Cruise Option Chicago City Tour with Architecture River Cruise Option](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0a/b0/a0/1f.jpg)
Chicago City Tour with Architecture River Cruise Option
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Chicago
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Superb632 reviews4.8
Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tou....
Lake Michigan Fireworks Cruise in Chicago
No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every Wednesday and Saturday night with an unobstructed 360-degree view of this e... More
![Lake Michigan Fireworks Cruise in Chicago Lake Michigan Fireworks Cruise in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/68/d2/db.jpg)
Lake Michigan Fireworks Cruise in Chicago
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Chicago
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Exellent89 reviews4.1
No city embraces summer quite like Chicago. Join in the celebration with friends and family on this ....
Private 45-Minute Chicago Skyline Helicopter Tour
This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is... More
Private Tour
![Private 45-Minute Chicago Skyline Helicopter Tour Private 45-Minute Chicago Skyline Helicopter Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0c/02/6d/0b.jpg)
Private 45-Minute Chicago Skyline Helicopter Tour
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Chicago
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Superb114 reviews4.8
This tour is unique as it offers the ability for you and two of your friends or family (a total of 3....
Private Tour
![Chicago Lakefront and Museum Campus Small-Group Segway Tour Chicago Lakefront and Museum Campus Small-Group Segway Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/ea/80/5e.jpg)
Chicago Lakefront and Museum Campus Small-Group Segway Tour
Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a scenic 6-7 mile Chicago Segway tour. Begin your adventure by gliding through the fragrant garden paths of Grant Park, where you'll ... More
Free Cancellation
Private Tour
(Saving 16% )
![Chicago Lakefront and Museum Campus Small-Group Segway Tour Chicago Lakefront and Museum Campus Small-Group Segway Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/ea/80/5e.jpg)
Chicago Lakefront and Museum Campus Small-Group Segway Tour
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Chicago
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Superb211 reviews5
Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a s....
Free Cancellation
Private Tour
(Saving 16% )
Chicago City Minibus Tour
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 a comfortable minibus, stopping at iconic locations like ear... More
Private Tour
![Chicago City Minibus Tour Chicago City Minibus Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0a/b0/a0/59.jpg)
Chicago City Minibus Tour
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Chicago
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Superb287 reviews4.9
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightse....
Private Tour
Chicago Small Group Food Tour
Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spo... More
Private Tour
![Chicago Small Group Food Tour Chicago Small Group Food Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/91/79/7e.jpg)
Chicago Small Group Food Tour
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Chicago
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Superb61 reviews4.7
Experience the best travel stories for yourself! Join a local expert and uncover hidden gems. Join u....
Private Tour
![Chicago Hauntings Original Ghost Bus Tour Chicago Hauntings Original Ghost Bus Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/9e/8e/28.jpg)
Chicago Hauntings Original Ghost Bus Tour
Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by the city's ghostlorist, Ursula Bielski. Ursula and her team of veteran paranormal researchers... More
Free Cancellation
Private Tour
(Saving 25% )
![Chicago Hauntings Original Ghost Bus Tour Chicago Hauntings Original Ghost Bus Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/9e/8e/28.jpg)
Chicago Hauntings Original Ghost Bus Tour
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Chicago
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Very Good131 reviews3.7
Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago....
Free Cancellation
Private Tour
(Saving 25% )
Chicago Seadog Fireworks Cruise
Enjoy Chicago’s iconic skyline at night and a fireworks display, with an exciting cruise on Lake Michigan. Experience a speedboat tour with a pause to enjoy the Navy Pier fireworks show. Our open-aired vessels provide uninterrup... More
Private Tour
![Chicago Seadog Fireworks Cruise Chicago Seadog Fireworks Cruise](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/0f/46/22/ed.jpg)
Chicago Seadog Fireworks Cruise
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Chicago
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Superb15 reviews4.6
Enjoy Chicago’s iconic skyline at night and a fireworks display, with an exciting cruise on Lake M....
Private Tour
Private Speakeasy Pub Crawl in Chicago with Local Historian
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 night out on the town to celebrate life and your friends. Hosted by a local... More
Skip The Line
Private Tour
![Private Speakeasy Pub Crawl in Chicago with Local Historian Private Speakeasy Pub Crawl in Chicago with Local Historian](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/81/90/82.jpg)
Private Speakeasy Pub Crawl in Chicago with Local Historian
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Chicago
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Superb7 reviews4.7
Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or....
Skip The Line
Private Tour
Chicago River Architectural Lunch Cruise
Experience the best of Chicago with a Premier Plus Architectural Lunch Cruise and spend your afternoon on the Chicago River with dining, picturesque views, and a narrated architectural tour of the city. While onboard, you’ll enj... More
Skip The Line
Private Tour
![Chicago River Architectural Lunch Cruise Chicago River Architectural Lunch Cruise](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/1f/2c/7c.jpg)
Chicago River Architectural Lunch Cruise
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Chicago
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Exellent28 reviews4.1
Experience the best of Chicago with a Premier Plus Architectural Lunch Cruise and spend your afterno....
Skip The Line
Private Tour
Chicago Walking Tour: Legacy of the Prohibition Era
Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots and try a local sweet treat along the way as you ex... More
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Private Tour
![Chicago Walking Tour: Legacy of the Prohibition Era Chicago Walking Tour: Legacy of the Prohibition Era](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/07/9a/76/36.jpg)
Chicago Walking Tour: Legacy of the Prohibition Era
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Chicago
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Superb74 reviews4.8
Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the....
Skip The Line
Private Tour
Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French, or Dutch.... More
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Private Tour
![Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/08/8a/ea/2c.jpg)
Your Way or the Highway: 2-hour Customized Private Walking Tour i....
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Chicago
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Superb32 reviews5
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you....
Skip The Line
Private Tour
Chicago Insider Segway Tour
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 totally weird stories of Chicago. We will travel back through the ages as you discover the city thro... More
Skip The Line
Private Tour
![Chicago Insider Segway Tour Chicago Insider Segway Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/db/7f/02.jpg)
Chicago Insider Segway Tour
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Chicago
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Superb51 reviews4.9
This is a tour like no other! Our newest Segway adventure is completely unique and will cover the go....
Skip The Line
Private Tour
2-Hour Haunted Segway Tour of Chicago
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 with your local guide, and see alleys, hotels, and sites of some of the most gruesome ... More
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Private Tour
![2-Hour Haunted Segway Tour of Chicago 2-Hour Haunted Segway Tour of Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/6e/df/ed.jpg)
2-Hour Haunted Segway Tour of Chicago
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Chicago
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Superb38 reviews4.7
Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on ....
Skip The Line
Private Tour
Chicago Pier Fireworks Segway Tour
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 while gliding through the park & lakefront on a Segway PT. View Buckingham Fountain's ... More
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Private Tour
![Chicago Pier Fireworks Segway Tour Chicago Pier Fireworks Segway Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/6e/e0/10.jpg)
Chicago Pier Fireworks Segway Tour
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Chicago
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Superb31 reviews4.9
See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't s....
Skip The Line
Private Tour
2-Hour Chicago City Lights Evening Segway Tour
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 Lakefront trail on this illuminated night tour.. Glide to luminous Soldier Field, enjoy... More
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Private Tour
![2-Hour Chicago City Lights Evening Segway Tour 2-Hour Chicago City Lights Evening Segway Tour](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/6e/e0/1a.jpg)
2-Hour Chicago City Lights Evening Segway Tour
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Chicago
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Exellent15 reviews4.4
See Chi-Town in a brand new light by night on this City Lights Segway Tour. There’s nothing quite ....
Skip The Line
Private Tour
Private Al Capone Gangster Tour in Chicago
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 makes all of the infamous stops for our patrons. Visit the old stomping grounds of: ... More
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Private Tour
![Private Al Capone Gangster Tour in Chicago Private Al Capone Gangster Tour in Chicago](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-360x240/06/71/e6/19.jpg)
Private Al Capone Gangster Tour in Chicago
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Chicago
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Superb11 reviews4.6
Chicago and the history of the mob are synonymous when we look back at history. That’s why we prov....
Skip The Line
Private Tour