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Activities & Tours: Illinois

Private Sightseeing Tours

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Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)
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based on 109 reviews
See Details → Duration :45 minutes
From $849
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Art Institute of Chicago Skip-the-Line Guided Museum 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
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based on 144 reviews
See Details → Duration :2 hours 30 minutes
From $132.5
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Private Chicago 6-Hour Boat Tour with Captain

Our Mission: We are dedicated to curating exceptional boating experiences, offering day and night cruises, fireworks displays, and serene voyages along the Chicago River. Our goal is to share the magic of the city's waterways, blending the thrill of the open lake with the iconic skyline as a backdrop. What sets us apart: Nauti Chicago stands out for our commitment to personalized journeys. Whether it's cruising to popular spots like the Playpen, enjoying delectable meals onboard, or discovering hidden dining gems ashore, our charters promise an unforgettable blend of adventure and indulgence.
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based on 2 reviews
See Details → Duration :6 hours
From $2175
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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.
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based on 3 reviews
See Details → Duration :4 hours
From $480.26
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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.
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based on 26 reviews
See Details → Duration :2 hours
From $74
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Chicago River Architecture and History-Private Boat Tour

Discover Chicago by private boat with a local Chicagoan to highlight its fascinating history and architectural marvels along the way! Before we board, we’ll take a short walk in the Chicago Loop, a bustling area filled with gems like the ostentatious Marshall Field building, the stained-glass-domed Cultural Center, and the Chicago Theatre, adorned with its emblematic marquee. After arriving at the dock, you’ll board your own private boat and set sail along the Chicago River. As we glide along, your guide will point out some of the city’s most fascinating landmarks. Stare up in awe at Willis Tower, once the world’s tallest building. Spot Union Station, which you might recognize from several famous films. And gaze upon a behemoth Art Deco building so large it once had its own zip code! We’ll also pass by Wolf Point, formerly occupied by Native Americans and later by many of Chicago’s first commercial buildings. Afterwards, you might want to explore all these sites and more on foot!
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based on 12 reviews
See Details → Duration :2 hours 30 minutes
From $695
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Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list. 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.  The unique view of the Navy Pier fireworks from the water is an unforgettable experience!  Offered Saturday evening in season.  All charters are NON-SMOKING experiences.
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based on 6 reviews
See Details → Duration :2 hours
From $542.82
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Chicago Private Sunset Sail on Lake Michigan

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.  All charters are NON-SMOKING experiences.
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based on 21 reviews
See Details → Duration :2 hours
From $483.96
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Chicago Private Architecture Walking Tour

On this tour your guide will take you on a walk around Chicago’s historic Loop District where you will get to see some of the oldest skyscrapers in the world and we'll take you inside some of the city’s most influential and iconic buildings.Your guide will share the history of Chicago and explain the multiple architectural influences that helped shape the city's incredible skyline! Schedule: 10:00 AM Meet your guide at The Fine Arts Building 10:15 AM Visit the Marquette Building 10:30 AM Visit The Rookery 11:00 AM Visit The Palmer House 11:15 AM Visit The Sullivan Center 11:30 AM Lunch time! 12:00 PM Visit The Chicago Athletic Association hotel 12:15 PM Visit The Chicago Cultural Center 12:30 PM Visit the Wrigley Building and the Tribune Tower 1:00 PM End tour around the Wrigley Building
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See Details → Duration :3 hours
From $185
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Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  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.
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based on 181 reviews
See Details → Duration :3 to 4 hours
From $489
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Private Chicago Architecture Tour

Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis from here to Hong Kong. On our Chicago Architecture Tour, we’ll stop at and discuss: • Sears “Willis” Tower • The John Hancock Building • Gothic gems • Magnificent Mile notable locations • Historic brownstones • The Frank Lloyd Wright homes of Oak Park We offer a uniquely added value opportunity to view not only the outside, but also explore the inside of many of these infamous buildings. Our tour will satisfy the architecture style and structural tastes of the most discerning traveling.
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based on 5 reviews
See Details → Duration :3 hours
From $880
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Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

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. All charters are NON-SMOKING experiences.
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based on 3 reviews
See Details → Duration :2 hours
From $433.82
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Private Chicago Pedicab Tour through Lincoln Park

We offer custom tours completely unique in the city of Chicago. This tour is great for seeing the park with your family, a romantic date or a friends day out after brunch or dinner. History, architecture, photo opportunities, time in the park and the lakefront, this tour checks all the boxes. Enjoy the breeze as our tour guide drives you between each location in the open air motorized tricycle, this is also a great option for anyone with mobility impairment as we do all the moving for you! We cover the area of Lincoln Park but for a fee you 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.
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based on reviews
See Details → Duration :1 to 1 hours 10 minutes
From $90
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Private Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.
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based on 2 reviews
See Details → Duration :2 hours
From $300
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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.
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based on 6 reviews
See Details → Duration :1 to 2 hours
From $69.34