Top Chicago Private Sightseeing Tours

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.)

What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a 46-foot Private Yacht. Chicago's newest Harbor has been adorned with new playgrounds, swimming pools, food stands, and more. We will pick meet you here for the start of a wonderful day! After 31st harbor, we will board the amazing Italian Azimut Yacht for 4 hours of amazement. While others have ordinary boats and vessels, the Azimut is one of a kind. You won't find another in Chicago. Additionally, while others are sharing spaces with strangers, you have the luxury of your own Private Yacht for the day. We will cruise north and see the Planetarium, Shedd Aquarium, and Chicago's Skyline. Up the River, we will head to some of Chicago's finest restaurants and architecture for an hour of amazement. Only to end the day at one of Chicago's hot spots - The Chicago Play Pen. Swim, relax, listen to music and enjoy an hour together before we head back!

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

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.

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.

Explore over 40 million artifacts, including SUE, the world’s largest, most complete T. rex ever discovered! Discover 23 mummies in a recreated Egyptian tomb, our dazzling Gem Hall or journey to the powerful Aztec empire! Meet Maximo our newest titanosaur at over two stories tall! The health of our guests and staff is always our top priority and we welcome you back to safely explore nearly half a million square feet of open gallery space.

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 50%* off compared to buying individual attraction tickets. This multi-attraction pass, valid for 60 days after your first use, provides admission to your choice of up to seven attractions, tours or activities - all one one pass. Select from more than 25 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! With Go City you can see more, do more, and save more. *Savings based on sample itineraries on the Go City website

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of 24 Hour and 48 Hour tickets, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck.

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

Chicago CityPASS® — Discover Chicago's best attractions at one great price with an easy to use mobile ticket. Spend less, experience more. Save 48% or more on prepaid admission to 5 must-see attractions: • Shedd Aquarium • Skydeck Chicago Plus your choice of admission to 3 of the following attractions: • Field Museum • Art Institute of Chicago • Museum of Science and Industry • 360 CHICAGO Observation Deck • Adler Planetarium • Shoreline Sightseeing Architecture River Tour

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting. With mobile tickets, simply scan your phone for direct entry into the SkyDeck

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.

See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the sights. From the storied Magnificent Mile to the glamour of the Gold Coast, you’ll encounter the best of the Windy City. This private tour is available in Portuguese, English, or Spanish, and kicks off promptly at 9am.

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.

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.

Our Chicago Foodie Lovers Tour will take you to the most iconic and delicious spots in Chicago all in one day. If you are looking for a little bit of culture, great photos, and a ton of delicious food then this is the tour for you. The day will start with meeting with your friendly local guide. From there your tour will begin as you start your day walking throughout Chicago and dining at the most famous and delicious food spots in Chicago. This half-day tour will be fully packed with famous landmarks, yummy food and much much more! ==== Full schedule 11:00 AM - Meet your guide at the Grand subway station 11:05 AM - Taste a famous Portillos hotdog 11:45 AM - Enjoy an Al’s Italian Beef Sandwich 12:35 PM - Drool lover a Chicago favorite... deep dish pizza 1:25 PM - Take some Garrett's Popcorn to go 1:35 PM - Check out Tribune Tower and Wrigley Building 2:05 PM - Try the delicious Do-rite Donuts 2:20 PM - Walk to Buckingham Fountain 3:00 - Get dropped off at the Millennium Subway Station

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.

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.