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Top Chicago Private Sightseeing Tours

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Private Chicago Sunset Sail on Lake Michigan

Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
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  • 2 hours
  • Free Cancellation
From  
US$389,76
From  
US$389,76
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  • 2 hours
  • Free Cancellation

Private Chicago City Sights Helicopter Tour

You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.
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  • 15 minutes
  • Free Cancellation
From  
US$174,50
From  
US$174,50
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  • 15 minutes
  • Free Cancellation

Private Al Capone Gangster Tour in Chicago

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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  • 3 hours
  • Free Cancellation
From  
US$660,00
From  
US$660,00
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  • 3 hours
  • Free Cancellation

Private Navy Pier Fireworks Sail in Chicago

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.
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  • 2 hours
  • Free Cancellation
From  
US$445,76
From  
US$445,76
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  • 2 hours
  • Free Cancellation

NEW TO VIATOR

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

Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain! No strangers tag along. It’s just you, kicking back with some good friends, great food and awesome views! All cruises come with free pizza that you cook on the boat's special pizza grill.
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  • 2 hours
  • Free Cancellation
From  
US$279,00
From  
US$279,00
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  • 2 hours
  • Free Cancellation

NEW TO VIATOR

Millennium Park Photoshoot and Walking Tour

On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.
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  • 1 to 2 hours
  • Free Cancellation
From  
US$150,00
From  
US$150,00
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  • 1 to 2 hours
  • Free Cancellation

NEW TO VIATOR

Private City Tour (3-4 hours) - Vehicle, Driver and Guide included!

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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  • 3 to 4 hours
From  
US$379,00
From  
US$379,00
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  • 3 to 4 hours

NEW TO VIATOR

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

Amy Bizzarri, author of Discovering Vintage Chicago and 111 Places in Chicago That You Must Not Miss will take you on a fascinating journey to the timeless, classic spots that evoke the unique character of Chicago's Loop. It includes charming stories that tell you what each place is like now and how it got that way, from classic restaurants to shops and other establishments that still thrive today.Major landmarks on this tour include the Berghoff Restaurant, the Picasso sculpture in Daley Plaza, Macy's Department Store, The Chicago Theatre, The Chicago Cultural Center and Palmer House. The tour starts at The Art Institute of Chicago.The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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  • 50 minutes
From  
US$4,99
From  
US$4,99
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  • 50 minutes

NEW TO VIATOR

30 Minute Private Vacation Photography Session with Local Photographer in Chicago

Go beyond the selfies and smartphone shots—and walk away from your Chicago vacation with professional-quality photos—when you book this private photo shoot experience. Meet your professional photographer guide at a time and place of your choosing and practice your poses: they’ll capture upwards of 15 high-resolution digital photos of you and your party, with Chicago’s majestic scenery as your backdrop. Your guide will also share insider knowledge and tips about the Windy City’s key attractions and eateries.
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  • 30 minutes
  • Free Cancellation
From  
US$250,00
From  
US$250,00
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  • 30 minutes
  • Free Cancellation

NEW TO VIATOR

Chicago Private 15 Minute Helicopter Tour For Two

Get a bird’s eye view of Chicago’s famous architecture and historical landmarks on a Private Flight For 2 aboard our all new Enstrom 280FX. Vertiport Chicago VIP Helicopter Tours is pleased to offer the best view of Chicago on the city’s only Enstrom helicopters. The Enstrom 280FX is a two-passenger helicopter that features windows above, below and all around for virtually unobstructed sightseeing. Take in the unparalleled views of the city, while your pilot narrates fascinating facts about the history of Chicago’s famous landmarks. Our 12-15 minute flight will provide you with unmatched views of Chicago’s most famous sights, including: Willis (Sears) Tower, the Magnificent Mile, Millennium Park and more! Day or night tour options available at the same price – book now!
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  • 15 minutes
  • Free Cancellation
From  
US$520,00
From  
US$520,00
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  • 15 minutes
  • Free Cancellation

Private Chicago Craft Beer and Pizza Tour

Visit three of Chicago’s top craft breweries on a customizable 4-hour tour. Bring your own group of 4 to 11 people on this all-inclusive tour led by a private guide, who shares details about Chicago’s craft brewing scene. Choose the breweries you wish to visit, and pair those suds with an included pizza dinner as well. You’ll learn how these hand-crafted beers are produced, and tour one of the brewery facilities (if available). No need to worry about getting from place to place: Transportation and hotel pickup and drop-off has included, so all you'll have to worry about is which beer to try first.
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  • 3 hours
  • Free Cancellation
From  
US$99,00
From  
US$99,00
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  • 3 hours
  • Free Cancellation

Private Guided Tour by SUV for up to 4 Guests - International Languages

Explore stunning, trend-setting Chicago at your own pace—and in your own language. Choose from Arabic, French, Mandarin, Russian, and more, and get personalized attention from your own multilingual guide. Build your own itinerary using a tailor-made list of stops—from Lake Shore Drive and Millennium Park to under-the-radar local neighborhoods—and customize your own sightseeing trip just as you like it.
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  • 3 hours
From  
US$750,00
From  
US$750,00
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  • 3 hours

Private Chicago Architecture Tour

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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  • 3 hours
  • Free Cancellation
From  
US$660,00
From  
US$660,00
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  • 3 hours
  • Free Cancellation

Private Guided Tour of Chicago - Deluxe Coach for 12 - International Languages

Experience Chicago in style on a half-day tour in a luxury mini-bus with a private chauffeur. Choose from a themed itinerary—from the Loop to local sports—or ask your driver to customize the experience to match your group’s interests. Cruise the city’s streets with a group of up to 12 passengers and a professional guide who narrates the outing in the language of your choosing.
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  • 4 hours
From  
US$975,00
From  
US$975,00
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  • 4 hours

Chicago Romance Helicopter Tour

Have a date night to remember with this helicopter tour over Chicago. As well as the incredible views of the city, you can enjoy boarding the helicopter via a red carpet, listening to commentary so you understand what you’re seeing, and indulging in champagne and chocolates. Opt to ride during the day or night for spectacular and different views. This is an ideal tour for a proposal, celebration, or just to express your love.
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  • 15 minutes
  • Free Cancellation
From  
US$620,00
From  
US$620,00
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  • 15 minutes
  • Free Cancellation

Chicago Premiere Private Helicopter Tour for 4

See Chicago from the air during a deluxe private 30-minute helicopter tour that rolls out the red carpet for your party of up to four people. Ride in a helicopter equipped with multiple windows that provide superb views of Windy City landmarks such as Millennium Park, Magnificent Mile, Wrigley Field, and Willis (Sears) Tower. The pilot provides insightful commentary about the sights, and the ground staff ensure your comfort in the departure lounge before and after your scenic flight.
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  • 30 minutes
  • Free Cancellation
From  
US$1 039,00
From  
US$1 039,00
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  • 30 minutes
  • Free Cancellation

Private Chicago Highlights Driving Tour

Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
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  • 3 hours
From  
US$99,00
From  
US$99,00
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  • 3 hours

Private Guided Tour of Chicago by Deluxe Mini-Coach for up to 12 guests

See Chicago your way on this private guided tour. Up to 12 passengers can take part in this tour that features the parts of Chicago that you are most interested in. Your driver will take you to select points of interest, while your guide fills you in on the history and insider information of the sights--all at your speed, according to your preferences.
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  • 4 hours
From  
US$875,00
From  
US$875,00
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  • 4 hours

Chicago Pilot Experience

Try your hand at flying a helicopter with this exhilarating new flight adventure. Soar into the sky and enjoy a rare opportunity to operate the aircraft yourself. Take charge of the Guimbal Cabri G2, a two-seat helicopter with a unique cockpit that is specially designed to allow passengers behind the controls. See Chicago’s celebrated skyline from the air with this unusual sightseeing experience.
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  • 1 hour
  • Free Cancellation
From  
US$400,00
From  
US$400,00
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  • 1 hour
  • Free Cancellation

Chicago Private Helicopter Tour for 5

Fly high over Chicago on a private helicopter tour just for you and your group of up to five people. Look down on Soldier Field, the Magnificent Mile, Millennium Park, the former Sears Tower (Willis Tower), and more as you learn a bit about the history of the city's landmarks. This VIP-style experience starts and ends at the dedicated lounge area of the heliport.
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  • 30 minutes
  • Free Cancellation
From  
US$1 550,00
From  
US$1 550,00
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  • 30 minutes
  • Free Cancellation

Chicago Girls Getaway Luxury Shopping Experience

Enjoy a shopping experience in Chicago with provided transportation so you don't have to worry about carrying around all of your new purchases. In a private minicoach for just your group, a driver will take you to popular Chicago shopping spots such as upscale Lincoln Park or trendy Bucktown or Wicker Park. A guide will curate your day to suit your shopping preferences, whether fashion, home decor, wine, sweets, or gourmet food. The guide can also make a lunch reservation for you, if you wish (own expense). One small cooler of Champagne is permitted per group, but no other alcohol is allowed on board the minicoach.
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  • 7 hours
From  
US$995,00
From  
US$995,00
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  • 7 hours

Private Guided SUV Tour for up to 4 Guests

Experience Chicago with a private guide and seperate driver in a luxury SUV. The tour is fully customizable with different itineraries to suit your tastes and interests. Visit Wrigley Field, peruse Fulton Market, and bring your camera for famous skyline views. Then get of the beaten path and venture into local neighborhoods. This tour is ideal for visitors who value privacy and who are looking for a personalized experience.
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  • 3 hours
From  
US$650,00
From  
US$650,00
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  • 3 hours

Personal Travel and Vacation Photographer Tour in Chicago

Document your travels with professional, candid, photos from your trip to Chicago. Choose from a one or two-hour session in a variety of locations, Whether it’s a romantic getaway, a family vacation, or special occasion, capture the moments with a professional travel photographer by your side. Put the selfie stick away and work with your knowledgeable local photographer to find the perfect locations for your photos. You will be ale to access your digital gallery within five working days of the tour.
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  • 1 to 3 hours
  • Free Cancellation
From  
US$258,19
From  
US$258,19
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  • 1 to 3 hours
  • Free Cancellation

SPECIAL OFFER

Chicago Riverwalk Self-Guided Audio Tour Guide for iPhone and Android

Welcome to Chicago’s scenic Riverwalk. It's an open, pedestrian waterfront on the south bank of the main branch of the River. Riverwalk has restaurants, park-seating, and boat rentals.---- It is a GPS enabled professionally-narrated driving tour! This app offers a fully-guided experience - just like a local giving you a personalized, turn-by-turn, fully-guided tour. ---- What do you get?App for iPhone and AndroidONE TIME PASSWORD will be sent on successful booking ----- How does it work?Use the app and drive hands-free like Google maps. On approaching an attraction, it’s photo pops up & its audio story starts. Just like having a local guide sitting with you!. No worries about a human guide’s accent, volume, exaggeration, and tips.---- Why this tour guide? Easy to use: Simply follow the GPS map & the routing line. Fully Automatic & Hands-FreeTour at your own pace:
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  • 1 to 2 hours
From  
US$3,20
US$4,00
US$0,80 savings
From  
US$3,20
US$4,00
US$0,80 savings
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  • 1 to 2 hours


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(888) 651-9785
(888) 651-9785