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Top Chicago Private & Custom Tours

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22 Tours and Activities

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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
From
$660.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$660.00 USD

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
From
$660.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$660.00 USD

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
From
$174.50 USD
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  • Duration: 15 minutes
  • Free Cancellation
From
$174.50 USD

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
From
$389.76 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$389.76 USD

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
From
$750.00 USD
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  • Duration: 3 hours
From
$750.00 USD

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
From
$975.00 USD
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  • Duration: 4 hours
From
$975.00 USD

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
From
$660.00 USD
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  • Duration: 3 hours
  • Free Cancellation
From
$660.00 USD

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
From
$445.76 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$445.76 USD

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
From
$99.00 USD
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  • Duration: 3 hours
From
$99.00 USD

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
From
$875.00 USD
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  • Duration: 4 hours
From
$875.00 USD

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
From
$1,525.00 USD
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  • Duration: 30 minutes
  • Free Cancellation
From
$1,525.00 USD

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
From
$995.00 USD
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  • Duration: 7 hours
From
$995.00 USD

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
From
$650.00 USD
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  • Duration: 3 hours
From
$650.00 USD

NEW TO VIATOR

Chicago Like a Local: Customized Private Tour

Get to know Chicago on a whole new level with a “lokafyer” 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, how to get around the city, and what it means to be a Chicagoan. Leave the tour with inside knowledge to enhance the rest of your stay.
  • Duration: 2 to 6 hrs
  • Free Cancellation
From
$30.00 USD
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  • Duration: 2 to 6 hrs
  • Free Cancellation
From
$30.00 USD

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 hrs
  • Free Cancellation
From
$255.01 USD
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  • Duration: 1 to 3 hrs
  • Free Cancellation
From
$255.01 USD

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 hrs
From
$379.00 USD
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  • Duration: 3 to 4 hrs
From
$379.00 USD

120 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 120 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: 2 hours
  • Free Cancellation
From
$650.00 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$650.00 USD

60 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 60 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
  • Free Cancellation
From
$350.00 USD
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  • Duration: 1 hour
  • Free Cancellation
From
$350.00 USD

Private Chicago Highlights Tour 101 by Tesla or SUV

Discover Chicago's bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture.
  • Duration: 2 hours
  • Free Cancellation
From
$450.00 USD
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  • Duration: 2 hours
  • Free Cancellation
From
$450.00 USD

30 Minute Private Vacation Photography Session with Local Photographer in Chicago

Flytographer 30 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: 30 minutes
  • Free Cancellation
From
$250.00 USD
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  • Duration: 30 minutes
  • Free Cancellation
From
$250.00 USD

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 hrs
From
$175.00 USD
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  • Duration: 3 to 8 hrs
From
$175.00 USD

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
From
$500.00 USD
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  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
$500.00 USD


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