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Top Chicago Luxury Tours

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56 Chicago Luxury Tours

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You can reserve your spot today and pay when you're ready.Learn more

Chicago in a Day: Food, History and Architecture Combo TourHalf-day Tours

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Chicago in a Day: Food, History and Architecture Combo Tour

star-5
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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Booked by 248 travellers
Small group
  • 5 hours
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  • Free Cancellation
From  
USD102.30 
From  
USD102.30 
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  • 5 hours
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  • Free Cancellation

Chicago City Minibus Tour with Optional Architecture River CruiseBus Tours

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Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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Booked by 3,422 travellers
Small group
  • 2 to 4 hours
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  • Free Cancellation
From  
USD39.45 
From  
USD39.45 
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  • 2 to 4 hours
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  • Free Cancellation

Chicago Helicopter TourLuxury Tours

Chicago Helicopter Tour

star-4.5
On a daytime helicopter tour over Chicago, enjoy views of the city's famed architecture and other sights from the air. Fly over Willis Tower (the old Sears Tower), Wrigley Field, Lincoln Park, and more while a pilot provides commentary about the city as you go.
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Booked by 1,074 travellers
Small group
  • 12 to 15 minutes
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  • Free Cancellation
From  
USD154.99 
Price varies by group size
From  
USD154.99 
Price varies by group size
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  • 12 to 15 minutes
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  • Free Cancellation

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VIP: Architectural River Cruise and Chicago Helicopter TourLuxury Tours

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VIP: Architectural River Cruise and Chicago Helicopter Tour

star-4.5
Experience Chicago from the air and the water on this two-part tour that features a river cruise and a helicopter ride above the city. First, take a cruise down the Chicago River to learn about the architectural history of the town. Then, board a state-of-the-art helicopter and fly above the skyline. Both tours are fully narrated and pass landmarks including Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.
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Booked by 309 travellers
Small group
  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation
From  
USD195.00 
From  
USD195.00 
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  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation

Lonely Planet Experiences: River North Historical Food TourLuxury Tours

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Lonely Planet Experiences: River North Historical Food Tour

star-5
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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Booked by 13 travellers
Small group
  • 2 hours
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  • Free Cancellation
From  
USD60.96 
From  
USD60.96 
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  • 2 hours
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  • Free Cancellation

Best of Chicago: History & Culture Tour with Chocolate and PopcornLuxury Tours

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Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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Booked by 29 travellers
Small group
  • 2 hours 30 minutes
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  • Free Cancellation
From  
USD50.63 
From  
USD50.63 
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago City Minibus TourBus Tours

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Chicago City Minibus Tour

star-5
NOTE: WE ARE ONLY OPERATING PRIVATE TOURS UNTIL AT LEAST EARLY MAY, DUE TO COVID 19. 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 comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience. 
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Booked by 14 travellers
Small group
  • 2 hours
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  • Free Cancellation
From  
USD39.45 
From  
USD39.45 
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  • 2 hours
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  • Free Cancellation

Haunted and Gangster Tour in ChicagoLuxury Tours

Haunted and Gangster Tour in Chicago

star-5
Tired of boring tours? Looking for special haunted experience ? Discover the most famous gangster hangouts and crime scenes, haunted places and mystery stories. Enjoy sightseeing famous Al Capone’s speakeasy bar, dig in the Prohibition era during the Secret route in Downtown Chicago.You will hear untold stories and outlandish details It’s an adventure where you travel back in time as a mobster member. Come explore the hidden.
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Booked by 101 travellers
  • 1 hour 45 minutes
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  • Free Cancellation
From  
USD29.00 
From  
USD29.00 
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  • 1 hour 45 minutes
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  • Free Cancellation

VIP: Chicago Helicopter Flight with Dinner for TwoLuxury Tours

VIP: Chicago Helicopter Flight with Dinner for Two

Enjoy a special day out in Chicago with this tour that combines a helicopter tour and dinner for two at the Duck Inn. Fly high above the Windy City for epic aerial views and photo ops, accompanied by guided commentary. Upon landing, head to the Duck Inn, a pre-Prohibition era tavern, for an intimate dinner.
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Booked by 65 travellers
Small group
  • 1 to 3 hours
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  • Free Cancellation
From  
USD520.20 
per group
From  
USD520.20 
per group
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  • 1 to 3 hours
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  • Free Cancellation

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike TourBike & Mountain Bike Tours

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Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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Booked by 1,364 travellers
  • 4 hours
From  
USD79.99 
From  
USD79.99 
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  • 4 hours

Private Al Capone Gangster Tour in ChicagoHalf-day Tours

Private Al Capone Gangster Tour in Chicago

star-5
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
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Booked by 39 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD660.00 
per group
From  
USD660.00 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

VIP: Chicago Helicopter Tour Plus 360 Chicago Observation DeckAttraction Tickets

VIP: Chicago Helicopter Tour Plus 360 Chicago Observation Deck

star-4
Travelers who like to get to know a city by seeing it from above will love this tour. View Chicago’s long coastline from the seat of a helicopter, then take your time spotting each individual landmark from the observation deck at 360 Chicago. There will be opportunities to take lots of impressive photos. Choose between a daytime or nighttime tours, for unforgettable views at any time of day.
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Booked by 157 travellers
Small group
  • 1 to 3 hours
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  • Free Cancellation
From  
USD175.00 
From  
USD175.00 
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  • 1 to 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Lakefront and Museum Campus Segway TourLuxury Tours

Lakefront and Museum Campus Segway Tour

star-5
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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Booked by 432 travellers
Small group
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD79.06 
From  
USD79.06 
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Private Chicago Architecture TourHalf-day Tours

Private Chicago Architecture Tour

star-5
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
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Booked by 23 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD660.00 
per group
From  
USD660.00 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

20 Minute Chicago Helicopter Tour With Fireworks ShowLuxury Tours

20 Minute Chicago Helicopter Tour With Fireworks Show

Get a front row seat to Chicago’s fireworks display during a 25 to 30-minute helicopter ride above the Windy City.  The nighttime tour takes you over Navy Pier, the Loop, and North Side. Listen to in-flight commentary through a provided headset, which also mutes outside noise. Then, fly to Navy Pier and photograph the stunning fireworks from above before returning to the Earth.
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Booked by 23 travellers
Small group
  • 18 to 20 minutes
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  • Free Cancellation
From  
USD279.00 
From  
USD279.00 
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  • 18 to 20 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)Luxury Tours

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

star-5
Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
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Booked by 18 travellers
Private experience
  • 45 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD598.67 
per group
From  
USD598.67 
per group
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  • 45 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Private Haunted History of Chicago Ghost TourHalf-day Tours

Private Haunted History of Chicago Ghost Tour

Discover spooky stories in the Windy City on a private haunted history tour. Visit places with names such as the Murder Castle and Death Alley, and hear about Al Capone and the Old Congress Hotel. See all three locations on one tour that reveals fascinating details about historical events, and rumors of murder and mayhem in Chicago.
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Booked by 6 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD660.00 
per group
From  
USD660.00 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!Luxury Tours

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Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!

star-4.5
Set your own course on this private self-guided cruise along the Chicago River. You're the captain for your group of just eight people, steering the boat wherever you like and getting epic views of the towering buildings along the river. When the munchies hit, grill up the provided pizza on the boat's barbecue and dig in.
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Booked by 23 travellers
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD297.60 
per group
From  
USD297.60 
per group
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Odyssey Chicago River Architectural Lunch CruiseDay Cruises

Odyssey Chicago River Architectural Lunch Cruise

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.
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Booked by 39 travellers
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD101.86 
From  
USD101.86 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

2 HR Haunted Segway TourLuxury Tours

2 HR Haunted Segway Tour

star-4.5
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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Booked by 181 travellers
  • 2 hours
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  • Free Cancellation
From  
USD75.58 
From  
USD75.58 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

The Chicago Tour Half-day Tours

The Chicago Tour

star-5
Discover some of Chicago’s top attractions—and step off the tourist trail when you visit several of its heritage, locals-frequented neighborhoods—on this introductory, small-group tour. Meet your guide in the Loop, and set off on foot. You’ll spy major landmarks like the Rookery Building, will head to Chinatown for a cultural immersion and delicious dumplings, will glimpse historical architecture in the Prairie District, will explore beautiful Grant Park, and more.
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Booked by 40 travellers
  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD99.00 
From  
USD99.00 
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  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Architecture Walking Tour: Dazzling Interiors of the LoopLuxury Tours

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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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Booked by 335 travellers
  • 2 hours
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  • Free Cancellation
From  
USD30.00 
From  
USD30.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!Luxury Tours

LIKELY TO SELL OUT

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!

star-5
Step aboard an easy-to-maneuver pontoon boat for a private cruise on the Chicago River. You and your private group of up to nine people will enjoy having the boat to yourselves, as well as captaining the ship. You can choose your own itinerary and move at your own pace, pausing to cook the included pizza on the boat's built-in pizza grill.
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Booked by 76 travellers
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD318.94 
per group
From  
USD318.94 
per group
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Fireworks CruiseLuxury Tours

Chicago Fireworks Cruise

star-3.5
Step on board a cruise boat bound for the waters of Lake Michigan, enjoying the sunset from the boat deck. Step up to the cash bar for drinks and snacks and find a place on board for a view of the epic fireworks display. A boat on the lake is the best place for catching the full fireworks spectacle and making great photos and videos.
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Booked by 63 travellers
  • 2 hours to 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD39.00 
From  
USD39.00 
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  • 2 hours to 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation


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