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Top Chicago Private Sightseeing Tours

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46 results | All Chicago 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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  • 3 to 4 hours
From
$425.34
per group
From
$425.34
per group

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

Private Chicago Highlights Driving Tour

Private Chicago Highlights Driving 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

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

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

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.
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  • 7 hours
  • Free Cancellation
From
$288.00
per group
From
$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
$660.00
per group
From
$660.00
per group
Taking safety measures

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.
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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 Riverwalk Photo Shoot and Walking Tour

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

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
$427.28
per group
From
$427.28
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
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

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.
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  • 50 minutes
From
$5.34
From
$5.34

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

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
$200.00
per group
From
$200.00
per group

Chicago Instagram Walking Tour: Most Famous Spots (Private & All-Inclusive)

Chicago Instagram Walking Tour: Most Famous Spots (Private & All-Inclusive)

star-5
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
$249.00
Price varies by group size
From
$249.00
Price varies by group size
Taking safety measures

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
$200.00
per group
From
$200.00
per group

Your Way or the Highway: 2-hour Customized Private Walking Tour (EN - FR - NL)

Your Way or the Highway: 2-hour Customized Private Walking Tour (EN - FR - NL)

star-5
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

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.
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  • 1 to 3 hours
  • Free Cancellation
From
$301.85
per group
From
$301.85
per group

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

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
$189.00
per group
From
$189.00
per group
Taking safety measures

Private Tour: Secret Food Tours Chicago

Private Tour: Secret Food Tours Chicago

star-5
We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history. We will discover each facet of this unique city as we eat and explore Chicago's Loop District. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!
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  • 3 hours
From
$89.70
From
$89.70

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!
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$145.95
Price varies by group size
From
$145.95
Price varies by group size
Taking safety measures

Chicago Instagram Tour: Most Famous Spots (Private & All-Inclusive)

Chicago Instagram Tour: Most Famous Spots (Private & All-Inclusive)

If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around! The morning will start with a private pickup from your hotel by one of our friendly, local guides. From there your tour will begin as you start your drive in one of our comfortable and spacious vehicles. This full-day tour will be fully packed with famous landmarks, vintage architecture, secret spots and much much more! ==== Full schedule 10:00 AM – Pick up from Hotel 10:15 AM – Check out Buckingham Fountain 10:45 AM – Arrive at Michigan Avenue Bridge 11:15 AM – Awe at the Chicago Cultural Center 12:15 PM – See Cloud Gate and explore Millennium park 1:00 PM – Lunch time 2:00 PM – Go to Chicago Theater 2:30 PM – See Garfield Park Conservatory 3:00 PM – Check out the Greetings from Chicago mural 3:30 PM – Snap a cool pic outside of Wrigley Field 3:45 PM – Return to hotel 4:00 PM – Arrive at hotel
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$749.00
Price varies by group size
From
$749.00
Price varies by group size
Taking safety measures

Chicago Riverwalk Self-Guided Walking Tour

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city's 'Second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax, boat rentals, and theater-style seating for various performances. Other attractions along the Riverwalk include the Vietnam Veterans Memorial Plaza, and the McCormick Bridgehouse & Chicago River Museum and if you are lucky enough, see a bridge lift from inside the bridge house. This self-guided audio tour allows you to explore Chicago's wonders with maximum flexibility and value. Within 30 min, 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 arrive, drive to the Welcome Stop. Once there, launch the app and simply follow the instructions! Stick to our recommended route for the best experience. Uncertain Travel Date? The tour’s valid for 30 days from booking!
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  • 1 to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$6.00
From
$6.00
Taking safety measures

Chicago Foodie Lovers Tour (Private & All-Inclusive)

Chicago Foodie Lovers Tour (Private & All-Inclusive)

Our Chicago Foodie Lovers Tour will take you to the most iconic and delicious spots in Chicago all in one day. If you are looking for a little bit of culture, great photos, and a ton of delicious food then this is the tour for you. The day will start with meeting with your friendly local guide. From there your tour will begin as you start your day walking throughout Chicago and dining at the most famous and delicious food spots in Chicago. This half-day tour will be fully packed with famous landmarks, yummy food and much much more! ==== Full schedule 11:00 AM - Meet your guide at the Grand subway station 11:05 AM - Taste the famous Portillos hotdogs 11:45 AM - Enjoy an Al’s Italian Beef Sandwich 12:35 PM - Drool lover a Chicago favorite deep dish pizza 1:25 PM - Take some Garrett's Popcorn to go 1:35 PM - Check out Tribune Tower and Wrigley Building 2:05 PM - Try the delicious Do-rite Donuts 2:20 PM - Walk to Buckingham Fountain 3:00 - Get dropped off at the Millennium Subway Station
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$289.00
Price varies by group size
From
$289.00
Price varies by group size
Taking safety measures

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 Private Sightseeing Tours in Chicago are taking additional safety precautions?
Q:
What Private Sightseeing Tours in Chicago are good for avoiding crowds?