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Top Chicago Private Sightseeing Tours

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43 results | All Chicago Tours

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Chicago Private Tours

Chicago Private Tours

star-5
144
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.
More
  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$425.34
per group
From
$425.34
per group
Taking safety measures

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
17
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
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
14
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
Taking safety measures

Private Custom City Tour in Chicago

Private Custom City Tour in Chicago

star-4
1
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
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Private Chicago Architecture Tour

Private Chicago Architecture Tour

star-5
4
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
  • Taking safety measures
From
$660.00
per group
From
$660.00
per group
Taking safety measures

Chicago Foodie Lovers Private Tour

Chicago Foodie Lovers Private Tour

star-5
1
It isn’t a trip to Chicago without tasting deep-dish pizza—and this private tour for food lovers will introduce you to true Chicago-style pizza, plus other Windy City specialties. Meet your guide downtown, and be sure to come hungry: You’ll eat hot dogs, Italian beef sandwiches, pizza, donuts, and more. Along the way, see highlights like the Wrigley Building and Magnificent Mile, and learn more about the city’s history and culture.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$319.00
Price varies by group size
From
$319.00
Price varies by group size
Taking safety measures

Personal Travel and Vacation Photographer Tour in Chicago

Personal Travel and Vacation Photographer Tour in Chicago

star-5
1
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
$310.73
per group
From
$310.73
per group

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
38
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
  • Taking safety measures
From
$849.00
per group
From
$849.00
per group
Taking safety measures

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

star-5
18
Enjoy a private 2-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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$200.00
per group
From
$200.00
per group
Taking safety measures

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

star-5
20
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$153.70
Price varies by group size
From
$153.70
Price varies by group size

Private Chicago Highlights Driving Tour
Likely to Sell OutLikely to Sell Out

Private Chicago Highlights Driving Tour

star-5
14
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 Frida & Friends tour in Pilsen

Private Frida & Friends tour in Pilsen

star-5
4
Discover Pilsen and its local art, street art, food and people. We will visit a traditional bakery and taqueria and enjoy the art of many great local artists. And then there are the hundreds of cool murals in the neighborhood. We may even meet one of the street artists or stop by an artist studio (on request).
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$200.00
per group
From
$200.00
per group
Taking safety measures

Private Chicago Scavenger Hunt: Eastside Art Heist

Private Chicago Scavenger Hunt: Eastside Art Heist

star-4
4
Play a city game where you will follow clues to discover amazing places and local stories in Chicago. You’ll tour Chicago’s famous Millenium Park and learn about the iconic works of art that populate the area on your way to riches beyond your imagination. Are you up for an adventure in Chicago? Highlights: Explore Chicago’s beloved Millenium Park and surrounding campuses Enjoy breathtaking views of the city skyline and Lake Michigan Learn about the artwork and architecture that marked Chicago’s journey from the 20th to the 21st century Try a new type of experience, the perfect mix between a tour, an outdoor escape game, and a treasure hunt. The city game will take you about 1.5 hours to complete, but there’s no time limit that will allow you to go at your own pace. You won't need a guide, just download the app, go to the starting point, and begin the adventure.
More
  • 1 hour 35 minutes
  • Free Cancellation
  • Taking safety measures
From
$8.28
Price varies by group size
From
$8.28
Price varies by group size
Taking safety measures

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
3
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.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Private Speakeasy Pub Crawl in Chicago with Local Historian
Likely to Sell OutLikely to Sell Out

Private Speakeasy Pub Crawl in Chicago with Local Historian

star-4.5
3
Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Chicago Lakefront Electric Bike Tour

Chicago Lakefront Electric Bike Tour

star-5
3
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
  • Taking safety measures
From
$69.34
From
$69.34
Taking safety measures

Chicago Instagram Walking Tour (Private & All- Inclusive)

Chicago Instagram Walking Tour (Private & All- Inclusive)

star-5
2
Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour for you. The morning will start with meeting with your friendly local guide at the meeting point. From there your tour will begin as you start your day walking throughout Chicago and exploring the most famous locations in the city. This half-day tour will be fully packed with famous landmarks, vintage architecture, secretly located spots and much much more! ==== Full schedule 10:00 AM- Meet your Guide at the Grand Subway Station 10:10 AM- Walk along Magnificent Mile 10:20 AM- Stop at Wrigley Building & admire Tribune Tower 10:50 AM- Explore Pioneer Court 11:20 AM- Explore Millennium Park & see Cloud Gate 11:55 AM- Check out an Iconic fountain 12:20 AM- Chicago Riverwalk 1:00 PM- Explore Navy Pier 2:00 PM- Get dropped off by your guide at Millennium station
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$265.60
Price varies by group size
From
$265.60
Price varies by group size
Taking safety measures

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

star-5
2
Aviation fanatics can take to the skies and try flying an actual helicopter with this Schaumburg flight experience that's perfect for first-timers. You enjoy helpful advice from your instructor before taking the controls on a flight that whisks you past Sears Centre Arena, Woodfield Mall, and Boomers Stadium. With free parking, noise-canceling headphones, and one-on-one attention from the pilot, this beginner-friendly experience is a near-perfect way to try flying for yourself.
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  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$295.00
per group
From
$295.00
per group
Taking safety measures

Private Sightseeing Cruise in Chicago

Private Sightseeing Cruise in Chicago

star-5
2
What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a 46-foot Private Yacht. Chicago's newest Harbor has been adorned with new playgrounds, swimming pools, food stands, and more. We will pick meet you here for the start of a wonderful day! After 31st harbor, we will board the amazing Italian Azimut Yacht for 4 hours of amazement. While others have ordinary boats and vessels, the Azimut is one of a kind. You won't find another in Chicago. Additionally, while others are sharing spaces with strangers, you have the luxury of your own Private Yacht for the day. We will cruise north and see the Planetarium, Shedd Aquarium, and Chicago's Skyline. Up the River, we will head to some of Chicago's finest restaurants and architecture for an hour of amazement. Only to end the day at one of Chicago's hot spots - The Chicago Play Pen. Swim, relax, listen to music and enjoy an hour together before we head back!
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$1,750.00
per group
From
$1,750.00
per group
Taking safety measures

Chicago Millennium Park Self-Guided Walking Tour

Chicago Millennium Park Self-Guided Walking Tour

star-4
1
Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you like; pausing to explore further on your own. Take in the sights of the public art—including the famous "Cloud Gate," otherwise known to locals as "The Bean"—and hear the stories behind their creation. The GPS-enabled guide will stop and start the professional commentary automatically as you explore the area. Here's how it works: Within 30 mins, we'll send you two things: a unique password and an app. Download the app onto your phone and enter the password. Then download the tour inside. When you reach there, walk to the Millennium Park Welcome Center. Once there, launch the app and simply follow the instructions from there! No expiration — the tour is available from the minute you book until forever! This is not an entrance ticket to attractions along the route. Check pandemic rules & opening hours before your visit.
More
  • 20 to 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$6.00
From
$6.00
Taking safety measures

Private Haunted History of Chicago Ghost Tour

Private Haunted History of Chicago Ghost Tour

star-5
1
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
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Private Chicago Scenic Driving Tour

Private Chicago Scenic Driving Tour

star-5
1
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$268.00
per group
From
$268.00
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
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
$5.34
From
$5.34

Private Half Day Highlights of Chicago, with Hancock Tower Observation Deck Tix

Private Half Day Highlights of Chicago, with Hancock Tower Observation Deck Tix

star-5
1
Enjoy a privately guided walking tour of Chicago's highlights, including a deep dish pizza and tickets to the 360 Observation Deck on the 94th floor of Hancock Tower. During your Private Half Day Highlights of Chicago Tour you'll visit the city's major sites. Known for its bold architecture and jazz heritage Chicago is a striking city whose skyline is dotted with skyscrapers including the Willis Tower and the neo-Gothic Tribune Tower. Your guide has plenty of stories to tell about this energetic city including how it's earned its many nicknames including the Second City and the City of Broad Shoulders. You'll get the chance to try the famous Chicago pizza and see for yourself why it's worldwide famous. Last but not least you'll visit the Hancock Tower’s Observation Deck, where you can enjoy the 360 degree views of the entire city.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$255.00
Price varies by group size
From
$255.00
Price varies by group size
Taking safety measures

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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?
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What Private Sightseeing Tours in Chicago are taking additional safety precautions?
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