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Top Chicago Private & Custom Tours

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Private Custom City Tour in Chicago

See Chicago the way you want to see it. This private tour is fully customizable to your specifications. Whether you are interested in the architecture and history, the art, the cool neighborhoods, or peaceful parks and happening beaches, this tour will cater to your tastes. Work with a guide to discover Chicago your way.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$660.00 USD
From  
$660.00 USD
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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.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
From  
$174.50 USD
From  
$174.50 USD
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NEW TO VIATOR

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

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 4 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.
  • Duration: 3 to 4 hours
  • Duration: 3 to 4 hours
From  
$379.00 USD
From  
$379.00 USD
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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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$445.76 USD
From  
$445.76 USD
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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.
  • Duration: 4 hours
  • Duration: 4 hours
From  
$975.00 USD
From  
$975.00 USD
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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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$660.00 USD
From  
$660.00 USD
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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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$389.76 USD
From  
$389.76 USD
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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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$129.00 USD
From  
$129.00 USD
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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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$750.00 USD
From  
$750.00 USD
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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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$660.00 USD
From  
$660.00 USD
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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.
  • Duration: 30 minutes
  • Free Cancellation
  • Duration: 30 minutes
  • Free Cancellation
From  
$1,039.00 USD
From  
$1,039.00 USD
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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.
  • Duration: 15 minutes
  • Free Cancellation
  • Duration: 15 minutes
  • Free Cancellation
From  
$620.00 USD
From  
$620.00 USD
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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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$99.00 USD
From  
$99.00 USD
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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.
  • Duration: 4 hours
  • Duration: 4 hours
From  
$875.00 USD
From  
$875.00 USD
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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.
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
$400.00 USD
From  
$400.00 USD
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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.
  • Duration: 30 minutes
  • Free Cancellation
  • Duration: 30 minutes
  • Free Cancellation
From  
$1,550.00 USD
From  
$1,550.00 USD
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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.
  • Duration: 7 hours
  • Duration: 7 hours
From  
$995.00 USD
From  
$995.00 USD
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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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
$650.00 USD
From  
$650.00 USD
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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.
  • Duration: 1 to 3 hours
  • Free Cancellation
  • Duration: 1 to 3 hours
  • Free Cancellation
From  
$264.18 USD
From  
$264.18 USD
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Chicago Like a Local: Customized Private Tour

Get to know Chicago on a whole new level with a friendly guide. Work together in advance to create a custom, private tour based on your interests, or leave the planning to your guide. Then go beyond the guide books and get know the city the way the locals do. Spend time exploring the neighborhood you are staying in - or go further afield -  and get an inside look at the best places to eat, local cultural events, and how to get around the city. Leave the tour with inside knowledge to enhance the rest of your stay.
  • Duration: 2 to 6 hours
  • Free Cancellation
  • Duration: 2 to 6 hours
  • Free Cancellation
From  
$30.00 USD
From  
$30.00 USD
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Chicago Fireworks Helicopter Tour

The dazzling Navy Pier Summer Fireworks show is held along Chicago’s waterfront every Sat and Wed throughout summer. On this tour, enjoy a spectacular aerial view of the fireworks as you soar over the pier in a helicopter. Feel like a VIP aboard a private helicopter; enjoy live on-board commentary as you fly over Millennium Park, Sears Tower, and Lake Michigan; and admire Chicago’s glittering skyline by night.
  • Duration: 30 minutes
  • Free Cancellation
  • Duration: 30 minutes
  • Free Cancellation
From  
$1,039.00 USD
From  
$1,039.00 USD
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Private Weekend Sailing Charter

Benefit from the flexibility of a private tour on a full-day excursion to attractions around Bali. Visit traditional villages and natural attractions such as Tegenungan waterfall and Mount Batur. Stop at a coffee plantation and Tegalalang village, which overlooks a hillside with rice terraces. Includes lunch, and transportation by air-conditioned vehicle.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$450.00 USD
From  
$450.00 USD
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NEW TO VIATOR

90 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 90 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos.The best souvenir ever.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
$500.00 USD
From  
$500.00 USD
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Chicago - Language Services - Interpretation and Translation

Basic, intermediate, and advanced interpretation services offered.  GMD Linguistics is a linguistic agency which offers certified translation, interpretation, transcription, voice-over/dubbing, subtitling, editing/proofreading, configuration, localization, web design and foreign language learning services. Price listed is all inclusive, no hidden fees.
  • Duration: 3 to 8 hours
  • Duration: 3 to 8 hours
From  
$175.00 USD
From  
$175.00 USD
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Book online or call
(888) 651-9785
(888) 651-9785