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Top Chicago Private Sightseeing Tours

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76 results | All Chicago Tours

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Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
38
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
From
US$483.96
per group
From
US$483.96
per group

Private 45-Minute Chicago Skyline Helicopter Tour
Likely to Sell OutLikely to Sell Out

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
91
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
From
US$849.00
per group
From
US$849.00
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
16
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
From
US$483.96
per group
From
US$483.96
per group

Skip-the-Line Art Institute of Chicago Exclusive Guided Museum Tour
Likely to Sell OutLikely to Sell Out

Skip-the-Line Art Institute of Chicago Exclusive Guided Museum Tour

star-5
82
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 30 minutes
  • Free Cancellation
From
US$115.54
Price varies by group size
From
US$115.54
Price varies by group size

Chicago Private Tours

Chicago Private Tours

star-5
167
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
  • Free Cancellation
From
US$489.00
per group
From
US$489.00
per group

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
9671
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
  • Free Cancellation
From
US$46.87
From
US$46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2814
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
  • Free Cancellation
From
US$42.00
From
US$42.00

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

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

star-5
404
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
  • Free Cancellation
From
US$108.08
From
US$108.08

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
1054
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
  • Free Cancellation
From
US$42.00
From
US$42.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
3532
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
  • Free Cancellation
From
US$35.00
From
US$35.00

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
367
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
  • Free Cancellation
From
US$27.00
From
US$27.00

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
248
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
From
US$68.00
From
US$68.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1313
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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  • 1 hour
  • Free Cancellation
From
US$44.99
From
US$44.99

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1698
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 to 2 hours
  • Free Cancellation
From
US$46.00
From
US$46.00

Chicago CityPASS

Chicago CityPASS

star-4.5
380
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, 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. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
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  • 9 days
From
US$114.00
From
US$114.00

Skydeck Chicago Admission Ticket
Likely to Sell OutLikely to Sell Out

Skydeck Chicago Admission Ticket

star-4
1075
Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower) with this pre-paid admission ticket. From the highest point in the city, look out on Chicago's skyline for panoramic views of the sprawling Windy City. Peruse the interactive displays and exhibits showcasing Chicago's history, which are geared toward curious learners of all ages. Then walk out on to the Ledge, a glass balcony that allows views of Navy Pier and Wrigley Field from one of the world's tallest buildings, standing 1,353 feet (412.4 meters) tall.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
US$44.00
From
US$44.00

Chicago Self-Guided Audio Tour

Chicago Self-Guided Audio Tour

star-4
7
Short and highly selective information in the audio commentary for top 15 tourist attractions in around Chicago Highlights of this Self-Guided Audio Tour • It allows you to go as per your own convenience of time, pace and location. • Simply use our personally created itinerary which starts from main train station of the city then gradually moves one by one (if required). • Not necessary to download any location tracking apps. It can be listened online in any devices (smartphones, tablets, laptops, etc.) • Available in multiple languages, you can choose the one you’re most comfortable with (should be selected at the time of booking) • It is one of the best options with lowest price for travelers who prefer flexibility on their tour. • If you have any questions about any attractions, No worries, we will answer in your language instantly.
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  • 1 to 6 hours
From
US$5.00
From
US$5.00

Private Chicago Highlights Driving Tour

Private Chicago Highlights Driving Tour

star-5
26
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
From
US$200.00
Price varies by group size
From
US$200.00
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
22
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
  • Free Cancellation
From
US$220.00
per group
From
US$220.00
per group

Chicago Lakefront Electric Bike Tour

Chicago Lakefront Electric Bike Tour

star-5
4
Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the Field Museum and Adler Planetarium, will zip right along the waters of Lake Michigan, and will stop to soak up picture-perfect views of the Chicago skyline.
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  • 1 to 2 hours
  • Free Cancellation
From
US$69.34
From
US$69.34

Private Chicago Tour with Driver and tour Guide. Hotel pick up included
Likely to Sell OutLikely to Sell Out

Private Chicago Tour with Driver and tour Guide. Hotel pick up included

star-5
3
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.
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  • 4 hours
  • Free Cancellation
From
US$497.18
Price varies by group size
From
US$497.18
Price varies by group size

Private Speakeasy Pub Crawl in Chicago with Local Historian

Private Speakeasy Pub Crawl in Chicago with Local Historian

star-4.5
4
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.
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  • 3 hours
  • Free Cancellation
From
US$880.00
From
US$880.00

Boat Tours through Chicago

Boat Tours through Chicago

star-5
1
This is a luxury million dollar yacht that you can enjoy for the day. We provide the captain and crew, you sit back and have a relaxing time while we show you Chicago from a side that most people never see. Enjoy some sights, have a glass of wine, go for a swim, propose! whatever you decide, we work for you and will do whatever we can do to make it s great day!!
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  • 2 to 8 hours
  • Free Cancellation
From
US$1,000.00
per group
From
US$1,000.00
per group

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
Likely to Sell OutLikely to Sell Out

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

star-5
2
Discover the best of the Windy City in just half a day on this private Chicago walking tour. Choose from multiple daily departure times, and meet your guide in Millennium Park. As you explore on foot, you'll learn about the city's history and spot highlights like the Magnificent Mile and Navy Pier. Finally, stop for a slice of deep-dish pizza before heading to the John Hancock Building's 360 Chicago observation deck.
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  • 3 hours
  • Free Cancellation
From
US$195.00
Price varies by group size
From
US$195.00
Price varies by group size

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What Private Sightseeing Tours in Chicago are 1 hour or less?
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