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Top Chicago Private Sightseeing Tours

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56 results | All Chicago Tours

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Chicago Private Tours

Chicago Private Tours

star-5
145
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
  • iconEnglish
  • Free Cancellation
From
US$425.34
per group
From
US$425.34
per group

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6992
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour
  • iconEnglish
  • Free Cancellation
From
US$40.33
From
US$40.33

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1343
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • iconEnglish
  • Free Cancellation
From
US$40.00
From
US$40.00

Chicago in a Day: Food, History and Architecture Combo Tour

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
165
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • iconEnglish
  • Free Cancellation
From
US$104.00
From
US$104.00

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
562
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • iconEnglish
  • Free Cancellation
From
US$40.00
From
US$40.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2183
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • iconEnglish
  • Free Cancellation
From
US$35.00
From
US$35.00

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
151
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • iconEnglish
  • Free Cancellation
From
US$26.00
From
US$26.00

45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
143
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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  • 45 minutes
  • iconEnglish
  • Free Cancellation
From
US$23.00
From
US$23.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
217
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
  • iconEnglish
From
US$59.00
From
US$59.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
916
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • iconEnglish
  • Free Cancellation
From
US$49.00
From
US$49.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1143
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • iconEnglish
  • Free Cancellation
From
US$46.00
From
US$46.00

Chicago CityPASS

Chicago CityPASS

star-4.5
335
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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  • 9 days
  • iconEnglish
  • Free Cancellation
From
US$109.00
From
US$109.00

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
  • iconEnglish
  • Free Cancellation
From
US$427.28
per group
From
US$427.28
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
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.
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  • 2 hours
  • iconEnglish
  • Free Cancellation
From
US$427.28
per group
From
US$427.28
per group

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
  • iconEnglish
  • Free Cancellation
From
US$465.00
Price varies by group size
From
US$465.00
Price varies by group size

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
  • iconEnglish
  • Free Cancellation
From
US$930.60
per group
From
US$930.60
per group

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
  • iconEnglish
  • Free Cancellation
From
US$319.00
Price varies by group size
From
US$319.00
Price varies by group size

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
  • iconEnglish
  • Free Cancellation
From
US$301.41
per group
From
US$301.41
per group

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
40
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
  • iconEnglish
  • Free Cancellation
From
US$849.00
per group
From
US$849.00
per group

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
22
The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.
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  • 2 hours to 2 hours 30 minutes
  • iconEnglish
  • Free Cancellation
From
US$153.70
Price varies by group size
From
US$153.70
Price varies by group size

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
Explore Chicago your way and on your own schedule on a private walking tour that's completely customized based on your interests. Whether you want to learn Windy City history or focus on architecture, street art, or Chicago's food scene, your local guide knows all the best places to see, shop, and dine. Plus, get plenty of personalized recommendations on where to go once the tour ends.
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  • 2 hours
  • iconEnglish
  • Free Cancellation
From
US$200.00
per group
From
US$200.00
per group

Private Chicago Highlights Driving Tour

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
  • iconEnglish
From
US$190.00
Price varies by group size
From
US$190.00
Price varies by group size

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
  • iconEnglish
  • Free Cancellation
From
US$200.00
per group
From
US$200.00
per group

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
  • iconEnglish
  • Free Cancellation
From
US$8.07
Price varies by group size
From
US$8.07
Price varies by group size

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