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Top Chicago Private Sightseeing Tours

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Private Chicago City Tour

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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    From
    US$425.34
    per group
    From
    US$425.34
    per group

    Great tour. Highly recommend

    Matthew and Harold were perfect tour guides. We learned all we needed to know for our first time in Chicago.

    ct2019623, Dec 2019

    52 Chicago Private Sightseeing Tours | All Chicago Tours

    Sort by:Featured

    45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

    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.
    More
    • 45 minutes
    • Free Cancellation
    • Taking safety measures
    From
    US$622.20
    per group
    From
    US$622.20
    per group
    Taking safety measures

    Chicago Highlights Driving Tour: Covid-19 Safe and Private Tour

    Chicago Highlights Driving Tour: Covid-19 Safe and 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.
    More
    • 3 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$190.00
    Price varies by group size
    From
    US$190.00
    Price varies by group size
    Taking safety measures

    Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

    Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

    star-5
    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
    • Taking safety measures
    From
    US$427.28
    per group
    From
    US$427.28
    per group
    Taking safety measures

    Millennium Park Photo Shoot and Walking Tour

    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.
    More
    • 1 to 2 hours
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

    Private Chicago Architecture Tour

    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.
    More
    • 3 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$660.00
    per group
    From
    US$660.00
    per group
    Taking safety measures

    Transfer to Chicago Premium Outlets

    Transfer to Chicago Premium Outlets

    star-5
    Spend a day shopping at the premier name brand shopping destination in the Chicago metro area, Chicago Premium Outlets. Featuring prominent international and American designer brands at discounted prices, you'll find deep discounts at stores like Nike, Armani, Calvin Klein, Kate Spade, 7 for All Mankind, and much more inside the outlet mall. The tour includes pickup and drop-off from Chicago hotels and five hours of on-the-ground shopping time.
    More
    • 7 hours
    • Free Cancellation
    From
    US$288.00
    per group
    From
    US$288.00
    per group

    Private Al Capone Gangster Tour in Chicago

    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
    • Taking safety measures
    From
    US$660.00
    per group
    From
    US$660.00
    per group
    Taking safety measures

    Navy Pier Photo Shoot and Walking Tour

    Navy Pier Photo Shoot and Walking Tour

    star-5
    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
    More
    • 1 to 2 hours
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

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

    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.
    More
    • 50 minutes
    From
    US$5.34
    From
    US$5.34

    Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

    Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

    star-5
    If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
    More
    • 2 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$427.28
    per group
    From
    US$427.28
    per group
    Taking safety measures

    Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

    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.
    More
    • 50 minutes
    From
    US$5.34
    From
    US$5.34

    Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)

    Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)

    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!
    More
    • 4 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$320.00
    per group
    From
    US$320.00
    per group
    Taking safety measures

    Lincoln Park Photo Shoot and Walking Tour

    Lincoln Park Photo Shoot and Walking Tour

    star-5
    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.
    More
    • 1 to 2 hours
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

    Museum Campus Photo Shoot and Walking Tour

    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.
    More
    • 1 hour
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

    Chicago Lakefront Electric Bike Tour

    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.
    More
    • 1 to 2 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$69.34
    From
    US$69.34
    Taking safety measures

    Private Segway Tour of Chicago

    Private Segway Tour of Chicago

    star-5
    There's no better way to tour the world-class city of Chicago than on a Segway! On your very own private tour, we will cruise around the parks and along Michigan avenue and show you the best that Chicago has to offer. If you are passionate about history, architecture, hauntings, Al Capone, and gangster or more, just let us know! We will customize the tour to fit your interests!
    More
    • 2 hours to 2 hours 30 minutes
    • Free Cancellation
    • Taking safety measures
    From
    US$145.95
    Price varies by group size
    From
    US$145.95
    Price varies by group size
    Taking safety measures

    Personal Travel and Vacation Photographer Tour in Chicago

    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.
    More
    • 1 to 3 hours
    • Free Cancellation
    From
    US$291.10
    per group
    From
    US$291.10
    per group

    Magnificent Mile Photo Shoot and Walking Tour

    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.
    More
    • 1 to 2 hours
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

    Chicago Riverwalk Photo Shoot and Walking Tour

    Chicago Riverwalk 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-hour private session with a professional photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours
    More
    • 1 hour
    • Free Cancellation
    From
    US$200.00
    per group
    From
    US$200.00
    per group

    Chicago Private Tour for Two: Lunch, Dessert, Drink Included

    Chicago Private Tour for Two: Lunch, Dessert, Drink Included

    This tour is a private tour for two people and is an overview of what makes Chicago so fascinating-the neighborhoods, history, architecture, culture, and foods. We will take you beyond the downtown loop to explore some of the great neighborhoods that make up this amazing and diverse city. The Chicago Tour will help you see the city without worrying about the logistics or the effort of planning. We will explore the Loop, Chinatown, South Loop/Prairie District, and end in Grant Park. Be prepared to walk a lot as we will explore by foot and use the public transit. Together we will see the city by going off the beaten path for a more authentic experience. Each tour will include all food and drinks (listed in the itinerary below) and an unlimited public transit day pass. You may add extra people for an additional $50pp. This must be arranged by emailing us. Also, we can adjust the itinerary based upon interests. All private tours will include lunch, dessert, and drink.
    More
    • 3 to 4 hours
    • Free Cancellation
    From
    US$375.00
    per group
    From
    US$375.00
    per group

    Private Haunted History of Chicago Ghost Tour

    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
    • Taking safety measures
    From
    US$660.00
    per group
    From
    US$660.00
    per group
    Taking safety measures

    Private Custom City Tour in Chicago

    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.
    More
    • 3 hours
    • Free Cancellation
    • Taking safety measures
    From
    US$660.00
    per group
    From
    US$660.00
    per group
    Taking safety measures

    Chicago City Tour

    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.
    More
    • 4 hours
    • Free Cancellation
    From
    US$405.34
    per group
    From
    US$405.34
    per group

    Frequently Asked Questions

    The answers provided below are based on answers previously given by the tour provider to customers’ questions.
    Q:
    What are the best Private Sightseeing Tours in Chicago?
    Q:
    What Private Sightseeing Tours in Chicago are 1 hour or less?
    Q:
    What tours in Chicago are taking additional safety precautions?
    Q:
    What tours in Chicago are good for avoiding crowds?

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