Chicago
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Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
5.0(70)
2 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$567
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Viator
Private Chicago History Museum Tour
Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.
5.0(18)
2 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$163
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Viator
Lincoln Park Zoo & Nature Museum Private Walking Tour
Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!
5.0(10)
2 Hours
Chicago
- Free cancellation
- Private tour
From
$275
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Viator
Private Chicago Foodie Tour
Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city landmarks such as the Tribune Tower, Wrigley Building, and Buckingham Fountain. Led by a friendly local guide, this experience blends Chicago’s most famous eats, rich culture, and great photo ops — the perfect way to enjoy the best of the Windy City in one delicious day. Tour Ticket Includes: • 1 Portillo’s hot dog • 1 small Garrett’s Popcorn • 6" Al’s Italian Beef Sandwich • 1 slice of authentic Chicago deep dish pizza
5.0(6)
4 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$288
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Viator
Private Chicago Guided Tour with Hotel Pickup
One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations. Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking. This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide. During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue. Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop. This private tour will finish off at your hotel in Chicago.
5.0(5)
4 Hours
Chicago
- Free cancellation
- Private tour
- Special offer
From
$794
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Viator
Self-Guided Chicago Loop Tour Explore the City at Your Own Pace
Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike
5.0(4)
2 Hours - 2h 30m
Chicago
- Free cancellation
- Private tour
From
$10
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Viator
Private Holiday City Tour
Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!
5.0(3)
3 Hours
Chicago
- Free cancellation
- Private tour
From
$499
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Viator
Private Wicker Park and Bucktown Walking Tour
This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city. The tour has 2 options: Wicker Park and Bucktown - faster pace, 2.5 miles of walking. Wicker Park only - slower pace, 1.5 miles of walking
5.0(3)
2h 30m
Chicago
- Free cancellation
- Private tour
From
$195
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Viator
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character. As you journey down the Magnificent Mile, you will learn how Chicago has earned each of its nicknames, including the City of Broad Shoulders, the Second City, and of course, the Windy City. Lastly, your guide will escort you to the Hancock Tower to bid on your adieus. You will then travel to the top of the Hancock Tower’s Observation Deck, where you can enjoy 360-degree views of the entire city at your own leisure.
5.0(3)
3 Hours
Chicago
- Free cancellation
- Private tour
From
$240
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Viator
Private City Tour 6-10ppl
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.
5.0(2)
3 Hours - 4 Hours
Chicago
- Free cancellation
- Private tour
From
$770
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Viator
Chicago 6-Hour City Tour by Sedan
Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city
5.0(2)
6 Hours
Chicago
- Free cancellation
- Private tour
From
$960
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Viator
4-Hour Chicago City Tour by SUV
Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city
5.0(2)
4 Hours
Chicago
- Free cancellation
- Private tour
From
$800
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Viator
Custom Chicago Walking Tours
We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s beer history, to local neighborhood food tours, every tour is crafted to be engaging, flavorful, and unforgettable.
5.0(2)
1 Hour - 3 Hours
Chicago
- Free cancellation
- Private tour
From
$20
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Viator
️ Chicago Instagram Walking Tour (Private & All- Inclusive)
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
5.0(2)
4 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$236
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Viator
Private Christmas Walking Tour in Chicago with Christkindlmarket
This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do European holiday customs shape winter traditions in American cities? Along State Street, seasonal décor reflects a long-standing retail heritage. The Christkindlmarket introduces a cultural tradition rooted in German history and craftsmanship. Wooden stalls and artisan goods echo centuries-old holiday markets of Europe. This experience blends festive atmosphere with cultural continuity in a refined city setting. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
5.0(1)
2 Hours
Chicago
- Free cancellation
- Private tour
From
$1,029
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Viator
The Bear Private Pedicab Food Tour of Chicago
If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The Bear and good food which is why we start our tour at the world famous Pequod's pizza where a hot pie will be ready waiting for us to pickup and try. Enjoy this in the pedicab as we begin our leisurely ride through the city getting an open air view of some of Chicago's cutest neighborhoods. Next up we go to Margies Candies for a Banana Split before embarking on a ride all the way from the west side to River North, crossing the Chicago River and getting some photos at the iconic LaSalle Flowers. End your epic Chicago adventure at Mr. Beef or Kasama! Your tour vehicle will be a decorated 6 seat pedicab driven by one of our knowledgeable tour guides. Comfortable for up to 4-5 adults, 6 if kids/teenagers are in the mix. Look at the photos of the cab and feel free to reach out with any questions.
5.0(1)
2 Hours - 3 Hours
Chicago
- Free cancellation
- Private tour
From
$200
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Viator
Private and All-Inclusive Tour of Chicago
Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in a spacious, air-conditioned vehicle, and let your friendly local guide show you the city’s most iconic sights and hidden gems. See top landmarks like Millennium Park, Cloud Gate (The Bean), Buckingham Fountain, the Chicago Cultural Center, and Wrigley Field, while discovering vintage architecture, vibrant neighborhoods, and photo-worthy murals along the way. This experience is fully private and customizable, giving you plenty of time for photos, exploring, or grabbing lunch at a local favorite. With insider stories, scenic stops, and seamless transportation, it’s the perfect way to see Chicago in one unforgettable day.
5.0(1)
6 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$750
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Viator
Personalized Private Driving Tour of Chicago for 1-3 People
Looking for a convenient way to see Chicago rain or shine? Discover Chicago and its remarkable landmarks in a unique way with a private tour designed just for you. Enjoy the comfort of a private car as a friendly local guide takes you through the city’s iconic architecture, vibrant neighborhoods, and scenic drives. This tour allows you to explore at your own pace while receiving insider tips and local insights. - Private tour for 1-3 people with a local guide - Explore iconic landmarks and vibrant neighborhoods - Flexible itinerary tailored to your interests - Enjoy the comfort of a private car with scenic drives
5.0(1)
3 Hours - 4 Hours
Chicago
- Private tour
From
$395
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Viator
Lincoln Park Secrets: Private Enchanted Pedicab History Tour
Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility impairment as we do all the moving for you! History, architecture, photo opportunities, time in the park and the lakefront, this tour checks all the boxes as we take you to all of our favorite spots. You will walk away with great memories and our guide will be sure to help you capture them. We cover the area of Lincoln Park but can extend your tour and see nearly anything in Chicago you would like to see. Examples include our Save Ferris tour package that recreates Ferris Bueller's Day Off complete with stops at Wrigley Field, Chicago River and The Chicago Art Institute or our Food Tour based of Hulu's hit Chicago show The Bear!
5.0(1)
1 Hour - 1h 10m
Chicago
- Free cancellation
- Private tour
From
$125
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Viator
Chicago Highlights Private Walking Tour with a Guide
Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.
5.0(1)
2 Hours
Chicago
- Free cancellation
- Private tour
From
$131
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Viator
Frank Lloyd Wright Oak Park Architecture Tour from Chicago
Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.
5.0(1)
5 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$226
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Viator
Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit
Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923. You are a detective in Chicago and a woman has been found murdered. It’s now up to you to to solve the crime and finde the culprit. After your purchase, you go to the designated pickup point and collect the mystery package containing everything you will need to solve this mystery. When you have collected it, you are free to begin whenever you want. Enjoy the flexibility of starting and stopping as you please. Solving this murder mystery is an exciting and challenging activity that you can try together with your family, friends, or colleagues. You must be a minimum of 2 people to buy this. A good tip! We recommend 2-4 in a group. Note that this is only Available in english.
5.0(1)
1 Hour
Chicago
- Free cancellation
- Private tour
From
$59
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Viator
Private Art Institute of Chicago Skip-the-Line Guided Tour
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive 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
5.0(297)
2h 30m
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$90
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Viator
Art Institute of Chicago Private Expert Guided Tour
Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultures, from classical masterpieces to cutting-edge contemporary works. Our expert guides will illuminate the stories behind each brushstroke, sculpture, and masterpiece, providing a rich narrative that breathes life into the art.
5.0(96)
2 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$215
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