Recent Searches
Clear
icon_solid_phone
Questions? (888) 651-9785(888) 651-9785
To limit the spread of the coronavirus, attractions may be closed or have partial closures. Please consult government travel advisories before booking. The WHO is closely monitoring the coronavirus and more information can be found here.

Top Chicago Private Sightseeing Tours

Category
Filter
Select Dates
Today
Tomorrow




All Experiences

43 Chicago Private Sightseeing Tours

Sort by:Featured

Did you know?You can reserve your spot today and pay when you're ready.
Learn more
Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Private City Tour (3-4 hours) - Vehicle, Driver and Guide included!Private Sightseeing Tours

Private City Tour (3-4 hours) - Vehicle, Driver and Guide included!

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.
...  More
Booked by 67 travellers
Private experience
  • 3 to 4 hours
From  
US$425.34 
per group
From  
US$425.34 
per group
Learn More
  • 3 to 4 hours

Private Chicago City Sights Helicopter TourPrivate Sightseeing Tours

LIKELY TO SELL OUT

Private Chicago City Sights Helicopter Tour

star-4.5
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.
...  More
Booked by 209 travellers
Private experience
  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$408.00 
From  
US$408.00 
Learn More
  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Booked by 20 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Reserve Now & Pay Later
Secure your must-do activities without being locked in
Private Chicago Highlights Driving TourHalf-day Tours

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.
...  More
Booked by 25 travellers
Private experience
  • 3 hours
From  
US$190.00 
Price varies by group size
From  
US$190.00 
Price varies by group size
Learn More
  • 3 hours

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.
...  More
Booked by 39 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Booked by 23 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Private experience
  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$405.34 
per group
From  
US$405.34 
per group
Learn More
  • 4 hours
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Private experience
  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$640.00 
per group
From  
US$640.00 
per group
Learn More
  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

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
Booked by 11 travellers
Private experience
  • 50 minutes
From  
US$5.34 
From  
US$5.34 
Learn More
  • 50 minutes

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

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

star-4
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
Booked by 18 travellers
Private experience
  • 50 minutes
From  
US$5.34 
From  
US$5.34 
Learn More
  • 50 minutes

PRIVATE Chicago City Mini Bus Tour. TEMPORARY LOW LOW PRICE!Day Cruises

PRIVATE Chicago City Mini Bus Tour. TEMPORARY LOW LOW PRICE!

The only way to travel with Covid 19 in the air. Sanitized vehicles with JUST YOUR GROUP! Don’t miss Chicago’s famous sights 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.  The city tour ends at Millennium Park. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking.
...  More
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$200.00 
per group
From  
US$200.00 
per group
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Lakefront Electric bike TourBike & Mountain 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.
...  More
Private experience
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$69.34 
From  
US$69.34 
Learn More
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Tour: Secret Food Tours ChicagoHalf-day Tours

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!
...  More
Private experience
  • 3 hours
From  
US$89.70 
From  
US$89.70 
Learn More
  • 3 hours

Millennium Park Photo Shoot and Walking TourLuxury Tours

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
Booked by 10 travellers
Private experience
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$160.00 
per group
From  
US$160.00 
per group
Learn More
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Museum Campus Photo Shoot and Walking TourLuxury Tours

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
Private experience
  • 1 hour
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$160.00 
per group
From  
US$160.00 
per group
Learn More
  • 1 hour
  • Reserve Now & Pay Later
  • Free Cancellation

Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!Luxury Tours

LIKELY TO SELL OUT

Private 2-hour boat rental aboard New York Style for 8 people ~ Free pizza!

star-4.5
Set your own course on this private self-guided cruise along the Chicago River. You're the captain for your group of just eight people, steering the boat wherever you like and getting epic views of the towering buildings along the river. When the munchies hit, grill up the provided pizza on the boat's barbecue and dig in.
...  More
Booked by 23 travellers
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$297.60 
per group
From  
US$297.60 
per group
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Booked by 6 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Weekend Sailing CharterSailing Trips

Private Weekend Sailing Charter

star-5
Benefit from the flexibility of a private tour on a full-day excursion to attractions around Bali. Visit traditional villages and natural attractions such as Tegenungan waterfall and Mount Batur. Stop at a coffee plantation and Tegalalang village, which overlooks a hillside with rice terraces. Includes lunch, and transportation by air-conditioned vehicle.
...  More
Booked by 10 travellers
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$450.00 
per group
From  
US$450.00 
per group
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!Luxury Tours

LIKELY TO SELL OUT

Private 2-hour boat rental aboard Deep Dish for 9 people ~ Free pizza!

star-5
Step aboard an easy-to-maneuver pontoon boat for a private cruise on the Chicago River. You and your private group of up to nine people will enjoy having the boat to yourselves, as well as captaining the ship. You can choose your own itinerary and move at your own pace, pausing to cook the included pizza on the boat's built-in pizza grill.
...  More
Booked by 76 travellers
Private experience
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$318.94 
per group
From  
US$318.94 
per group
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)Luxury Tours

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
Booked by 18 travellers
Private experience
  • 45 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$598.67 
per group
From  
US$598.67 
per group
Learn More
  • 45 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Magnificent Mile Photo Shoot and Walking TourLuxury Tours

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.
...  More
Booked by 6 travellers
Private experience
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$160.00 
per group
From  
US$160.00 
per group
Learn More
  • 1 to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

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.
...  More
Booked by 13 travellers
Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$105.60 
From  
US$105.60 
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Fireworks Cruise ~ 2.5-hour boat rental for 8 people ~ Free pizza!Luxury Tours

LIKELY TO SELL OUT

Private Fireworks Cruise ~ 2.5-hour boat rental for 8 people ~ Free pizza!

Rent with us and you can take a private, self-guided cruise along the Chicago River where you’re the captain! No strangers tag along. It’s just you, kicking back with some good friends, great food and awesome views! All cruises come with free pizza that you cook on the boat's special pizza grill. For more information call 1-770-PONTOON.
...  More
Private experience
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$404.27 
per group
From  
US$404.27 
per group
Learn More
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Great Lakes Explorer Classic AmericanaMulti-day Tours

Great Lakes Explorer Classic Americana

This 8-day small group journey from Chicago takes you around and across Lake Michigan. From the architecture and music of Chicago to going back in time on Mackinac Island, the Great Lakes region truly is a magical experience. American Experiences small group, multi-day tours provide you with authentic, in-depth experiences not found elsewhere. Your trip includes more than just the basics-- a welcome reception, one or two unique specialty meals, three and four star quality boutique hotels, multiple guided tours with opportunities to choose your activity as well as free independent exploration, and transportation. Plus, our knowledgeable tour guide stays with you for the duration of the trip and can personalize your experiences to meet the needs of both you and the group. Get to know like-minded people from all over the world who enjoy similar experiences and enrich your appreciation of America's magical Great Lakes with American Experiences small group tours .
...  More
Private experience
  • 8 days
From  
US$4,464.00 
Price varies by group size
From  
US$4,464.00 
Price varies by group size
Learn More
  • 8 days


icon_solid_phone
Book online or call
(888) 651-9785
(888) 651-9785