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Top Chicago Private Sightseeing Tours

Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

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Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

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50 Chicago Private Sightseeing Tours | All Chicago Tours

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Private Chicago City Tour City Packages

Private Chicago City Tour

star-5
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
$425.34
per group
From
$425.34
per group

Private Custom City Tour in ChicagoHalf-day Tours

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.
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  • 3 hours
  • Free Cancellation
From
$660.00
per group
From
$660.00
per group

Chicago Highlights Driving Tour | Covid-19 safe & PRIVATE tourHalf-day Tours

Chicago Highlights Driving Tour | Covid-19 safe & PRIVATE tour

star-5
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
  • Free Cancellation
  • Taking safety measures
From
$190.00
Price varies by group size
From
$190.00
Price varies by group size
Taking safety measures

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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  • 3 hours
  • Free Cancellation
From
$660.00
per group
From
$660.00
per group

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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  • 3 hours
  • Free Cancellation
From
$660.00
per group
From
$660.00
per group

Tour of Chicago and the SuburbsFull-day Tours

Tour of Chicago and the Suburbs

We invites you to discover Chicago. Our private tours cater to each group’s interests, including themes such as architecture, history, culture, sports, and shopping. Each tour is customized to fit your interests and includes an expert guide, luxury vehicle, and driver. We working for clients that are looking for more than the one-size-fits-all tour. Representatives of our company will meet you and your family, friends (all companions) at the airport - warmly and without delay. For first-time visitors to Chicago, especially those with a tight schedule, this is the private tour of Chicago for you. The tour views primary tourist attractions like Navy Pier, Millennium Park, Lincoln Park, Magnificent Mile, Museum Campus, the Water Tower, the lakefront, and downtown’s skyline. You’ll learn about the Great Chicago Fire, the growth of Chicago around the turn of the last century, its power as a hub for communications and industry, and its magnificent architecture.
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  • 8 hours
  • Free Cancellation
From
$640.00
per group
From
$640.00
per group

Chicago City TourHalf-day Tours

Chicago City Tour

Discover Chicago and its historic Architecture, Vibrant Neighborhoods, Parks, Museums, Lakefront and more! Let the Windy City carry you away as you explore Chicago top to bottom, scoping out the city's must-see parks, can't-miss lake views, and iconic architecture on this half-day tour. From the Loop to Lincoln Park, keep your camera at the ready—Chi-town's a charmer! Begin your ride through the skyscrapers of the Loop. Watch for fly balls popping high over Wrigley Field, check out the Picasso sculpture in Richard J. Daley Square, and cross over the Chicago River on one of the city's iconic bridges. Ride along almost the entire length of the scenic Outer Drive, enjoy a verdant respite in the urban oasis of Grant Park, and keep your eyes toward the sky as you admire the John Hancock Building, listening to the history behind State Street and the Magnificent Mile.
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  • 4 hours
  • Free Cancellation
From
$405.34
per group
From
$405.34
per group

Private Chicago City Mini Bus TourDay Cruises

Private Chicago City Mini Bus Tour

Don’t miss Chicago’s famous sights (now including Wrigley Field!) and fabulous views on this award-winning private 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 beautiful attractions. Your private tour ensures a more personal experience. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking. The best way to tour at this time! Sanitized vehicles with just your group.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$200.00
per group
From
$200.00
per group
Taking safety measures

Millennium Park Photo Shoot and Walking TourCity Packages

Millennium Park Photo Shoot and Walking Tour

star-5
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
$160.00
per group
From
$160.00
per group

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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  • 3 hours
  • Free Cancellation
From
$660.00
per group
From
$660.00
per group

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)City Packages

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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  • 45 minutes
  • Free Cancellation
From
$598.67
per group
From
$598.67
per group

Museum Campus Photo Shoot and Walking TourCity Packages

Museum Campus Photo Shoot and Walking Tour

star-5
Enjoy a private portrait session with your own professional photographer during this VIP shoot in Chicago. Discover top landmarks in the city as you follow a photogenic, pre-planned route, with backdrops such as the Adler Planetarium, the Field Museum, and the Shedd Aquarium. Then, receive a digital portrait gallery of edited images within just one to two days.
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  • 1 hour
  • Free Cancellation
From
$160.00
per group
From
$160.00
per group

Private Chicago Craft Beer and Pizza TourHalf-day Tours

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
$105.60
From
$105.60

Personal Travel and Vacation Photographer Tour in ChicagoCity Packages

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
$282.28
per group
From
$282.28
per group

Magnificent Mile Photo Shoot and Walking TourCity Packages

Magnificent Mile Photo Shoot and Walking Tour

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours --1-hour session includes 15 digital images --2-hour session includes 25 digital images -Edited images delivered to your email within 24-48 hours from your tour *Allow us to share photos from your tour on our website and social media and we will include 10 extra downloads in your online gallery. *Additional photos and prints can be purchased through your online gallery.
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  • 1 to 2 hours
  • Free Cancellation
From
$160.00
per group
From
$160.00
per group

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMapCity Packages

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

star-1
Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.
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  • 50 minutes
From
$5.34
From
$5.34

Frank Lloyd Wright Architectural Tour - Private Luxury Vehicles - All InclusiveHalf-day Tours

Frank Lloyd Wright Architectural Tour - Private Luxury Vehicles - All Inclusive

This is a drive by tour, no tour guide included, admission not included. Choose the number of hours & the vehicle type and we can help you make the most out of our time. Book a VIP treatment to enjoy this architectural tour in your private car. Stop at any of the sites and take as many pictures as you like. The actual tour hours may vary due to traffic conditions. Each tour starts when we pick you up and ends when we drop you off. Please take the travel time into consideration when booking a tour. It takes roughly 40 minutes between downtown Chicago and Oak Park. This is included in the 3 hours charter. You can combine this architectural tour with any other city tours that we offer. We are open 24/7, every day. Book today with the highest rated limousine service in Chicago! Call today to customize your tour.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$302.40
per group
From
$302.40
per group
Taking safety measures

Chicago Lakefront Electric Bike TourMountain Bike Tours

Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a chance to ride Electric Bikes and see the city from a different vantage point. It all begins navigating through Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus). As we admire the grounds and perfect location between the iconic skyscrapers and nature. We will then proceed and make our way over to the lakefront path. Riding along we will take you to a magnificent view of the skyline which is the best place for a photo shoot. Afterward, we will take the lakefront bike path over the Chicago River and past Navy Pier. A quick ride back to our starting point ends the tour.
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  • 1 to 2 hours
  • Free Cancellation
From
$69.34
From
$69.34

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMapCity Packages

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMap

star-4.5
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating guided tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. 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
$5.34
From
$5.34

Chicago - Language Services - Interpretation and TranslationPrivate Sightseeing Tours

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.
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  • 3 to 8 hours
From
$186.67
From
$186.67

Magic Christmas Tour in Illinois (Chicago)City Packages

Magic Christmas Tour in Illinois (Chicago)

The exclusive tour only in the Christmas period! This special times brings magic Chicago, Illinois. Chicago is known for being a architectural city from the slopes of the John Hancock center to the Boxy sides of the Willis tower. Together with the professional local guide, you will visit the most beautifully decorated places. You will feel spellbound with the charming atmosphere in the streets which you can feel only this time of the year! What is the story of the Christmas tree? Who was the first to decorate it in the world? What magical things can happen during the Christm as period? Have you heard about Christmas spells? You will hear miraculous Christmas legends about Chicago, Illinois. You will visit the old-fashioned Christmas Market in the city. What makes it so popular? What local products is must taste at Christmas? Fill your heart with the joy and experience magic Chicago, Illinois.
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  • 2 hours
From
$733.60
per group
From
$733.60
per group

West Loop Walking Craft Beer and Pizza TourPrivate Sightseeing Tours

West Loop Walking Craft Beer and Pizza Tour

Pair craft beer tastings at three of Chicago's finest breweries with a pizza dinner on this 4-hour walking tour in the Windy City. A guide leads your small group on a tour of the brewery scene in the vibrant West Loop of Chicago. Tour starts at the first stop on tour.  Guests can stay at final location if they decide to continue.  Actual tour will take from 3 to 4 hours.  All tasting fees and pizza meal is included in price.
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  • 4 hours
  • Free Cancellation
From
$105.60
From
$105.60

Private 4-hour Walking Tour - also available in French & Dutch Half-day Tours

Private 4-hour Walking Tour - also available in French & Dutch

star-5
Enjoy a private 4-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. Focus can be on public or street art, architecture, food and much more!
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  • 4 hours
From
$320.00
per group
From
$320.00
per group

The collection of 10 self-guided audio tours in Chicago with izi.TRAVEL AppCity Packages

The collection of 10 self-guided audio tours in Chicago with izi.TRAVEL App

This package allows you to save 30% compared to buying audio tours one by one: it consist of 10 self-guided audio tours on a variety of themes: classical city sightseeing tours / lifestyle tours about the best bars, restaurants and shops / an engaging journey through filming locations of famous movies, and many more. All tours have been created by professional publishers and guides: Time Out US, ListenUp, Entertainment tours, Audioviator, Travel Communications, Tim Richards. The tours differ in duration and walking distances: from one-hour walks to full day experiences. In different areas of the city: Millennium Park, Andersonville, Pilsen, Little Italy, Logan Square, Art Institute, and many more. These audio guides are GPS-triggered, which means you may start the tour and put your smartphone in your pocket – all audio stories will play automatically when you reach an attraction. Some tours also have a navigational tips, which will guide you where to go next.
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  • 1 to 4 hours
  • Free Cancellation
From
$37.34
From
$37.34

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