Best of Chicago Tour in Chicago, IL

See Sight Tours*HOTEL PICK-UP ONLY*Chicago, IL 60611
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Face masks are required. Temperature check for guests upon arrival. 

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Experience all the Chicago highlights in one tour! See the Famous Bean, the Chicago Skywalk, the Chicago Adler view point, and Buckingham Fountain. Your personal guide will be able to tell you all the ins and outs of the windy city and about the most famous landmarks. Enjoy a boat ride to experience some of Chicago’s best architecture from the water. Don’t forget to go way up high and experience the Sky Deck and the 360 Chicago Observation Deck. For an experience you won’t forget, make sure to participate in the coolest experience – Tilt! This tour is thrilling and will be sure to leave those who crave the most out of their visit to Chicago, satisfied!

up to 4 hrs 1 or more people

Good To Know

from Ashley, one of our Chicago Travel Experts
  • Pick-up and drop-off from downtown Chicago hotels.
  • The duration of the tour is 4.5 hours.
  • Operates in all weather conditions, dress appropriately.


from Best of Chicago Tour
Explore the Windy City with See Sight Tours, Chicago’s best small group tours (max. 7 guests).

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan. Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights, and personalized recommendations.

Begin your 4-hour small-group tour of Chicago with a complimentary downtown Chicago hotel pick up in the comfort and style of one of our Mercedes Metris vans where you will be escorted to your very first stop - Willis Tower.

No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere - Skydeck Chicago (formerly Sears Tower). Taking the elevator all the way up to the 103rd floor where you will enjoy a spectacular 360-degree view spanning 50 miles and 4 states. The most spectacular view - 1,353 feet down "Dare to Stand Out" on The Ledge - special glass balconies extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience.

Next, once your feet are back on solid ground your guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. As the mecca for American architects, Chicago’s skyline is one of the greatest and this viewpoint is the best place to marvel at the skyline of Lake Michigan.

Your guide will then take you to see the beauty of Chicago's architecture by seeing world-famous skyscrapers from the Chicago River. Aboard the Shoreline Architecture Cruise, you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments.

To finish your tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain, one of the largest fountains in the world, and the Chicago Bean (Cloud Gate) - British artist Anish Kapoor's first public outdoor work installed in the United States - both great locations to take great pictures.

At the end of your tour, your guide will take you back to your downtown Chicago hotel.

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Frequently Asked Questions about Best of Chicago Tour

Where does the tour start?

Pick up and drop off from hotels in downtown Chicago.

When will the guide pick me up for my tour?

We will email or call you 1-3 days prior to your tour to confirm a specific pick-up time. If you do not have access to phone or email, please be ready and waiting in the hotel lobby half an hour before your tour start time.

Do you have car seats available?

See Sight Tours does not provide car seats for children. By law, children less than 8 years of age can sit on an adult's lap and be buckled in during the tour. Should you wish to bring a car seat with you we ask that you let us know in advance so we can be prepared. Please note, if you do choose to bring a car seat with you, it is your responsibility to install and uninstall the seat at each stop on the tour.

How long is the tour?

The duration of the tour is 4.5 hours. Time varies depending on traffic.

Does the tour operate in inclement weather?

Yes, the tour operates in all kinds of weather, so dress appropriately. The boat cruise may be affected.

Is there anything not included in the price of the tour?

We recommend bringing extra cash to purchase food at stops or bringing snacks with you. Souvenirs and other items you may purchase on your tour are also not included in the price of your tour. Gratuities are optional and always appreciated.