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See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package — available nowhere else — provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.


  • Viator VIP package to the top Chicago sights including early access to Willis Tower
  • Gain early entry to the Skydeck in Willis Tower for magnificent views without the crowds!
  • Jump on a trolley for a guided tour of top Chicago attractions including the Hancock Center and the Field Museum
  • Admire gorgeous skyline views on a 75-minute cruise of the Chicago River
  • Sip on a complimentary drink as you learn about the city’s architecture
  • Don't miss this insider experience of the best of Chicago — it can't be booked anywhere else!

Recent Photos of This Tour

What You Can Expect

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

Viator VIP River Cruise

Head to Skydeck Chicago at Willis Tower (formerly Sears Tower) and enjoy exclusive early access to this interactive experience on the 103rd floor, an attraction that brings thousands of visitors a day. With this Viator VIP, you'll arrive before normal operating hours to covet uninterrupted views without the crowds. 

Learn fun facts from an audio tour and snap photos of Lake Michigan and city sights as you step onto the Ledge — a series of glass-and-steel cubes that protrude 4.3 feet (1.3 meters) from the Skydeck. Hovering 1,353 feet (1,353 meters) above the city, you’ll find yourself standing outside the tallest skyscraper in the Western Hemisphere.

After an hour here, take a 2-hour trolley tour of downtown Chicago with onboard narration about city history, architecture and landmarks. Motor along LaSalle Street in the Loop, and admire structures such as the Rookery Building. See glass-and-steel skyscrapers by Mies Van Der Rohe, the corncob-shaped towers in Marina City, and famous sculptures by Picasso, Calder, Miró and Chagall. 

Make a stop at Millennium Park, cross the drawbridge over the Chicago River and continue along the Magnificent Mile past the John Hancock Center, Tribune Tower, Wrigley Building, Grant Park, Soldier Field and the Field Museum of Natural History, before a stop at Adler Planetarium for awe-inspiring views of the Chicago skyline on the shores of Lake Michigan.

On arrival at Navy Pier, use your free time to grab lunch (own expense) before boarding the boat for a 1-hour Chicago River cruise. Learn from an architecture expert about notable landmarks while you drift past the IBM Building, Aon Center and Willis Tower — now viewed from the water. 
Finish your 5.5- to 6-hour VIP tour of Chicago back at Navy Pier, with plenty of time left in your day to explore on your own. 

Viator VIPs feature travel experiences not typically available to the general public — from behind- the-scenes access to private viewings and VIP service — at many of the world’s top attractions, often with no lines and no crowds. Viator VIP tours are not available from other 3rd-party online sellers.

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Customer Reviews


5 star rating: Highly Recommended November 2016

nice place for pictures

Patricia L

5 star rating: Highly Recommended October 2016

This was a great tour where we travelled round the main sights of beautiful Chicago. We began at the Willis Tower where I stood on the glass platform at a huge height, mainly because it was early morning and very misty! It was a great experience! From there, we went on the trolley bus tour round Chicago visiting all the major places of interest. The lady who drove the bus was also our guide, and she provided us with interesting information in a very knowledgeable and often humorous way. She was great! A highlight was our visit to the Millenium Park to see a sculpture called the Bean where we took pictures at every angle with a backdrop of the fabulous Chicago skyline. Following this, we went on a gorgeous boat trip on the Chicago River. Whilst enjoying a glass of wine, we admired the spectacular architecture and skyline of Chicago. We can definitely recommend this trip with all its variety, visiting the wonderful sights of this amazing city.

Nancy C

5 star rating: Highly Recommended October 2016

Everything went well, the booking went well, the tour guide was very friendly and knowledgeable. I just wish you would have had rain dates. When we got up in the Skydeck we really could not see anything. We were disappointed about that. It was our first time up there, plus there was no one to take our picture. Rain dates very important. Trolley and river cruise were wonderful.


5 star rating: Highly Recommended September 2016

being first on the line beating all queues going to the skydeck is an all star convenience considering i am touring with my mom on a wheelchair... overall, it's satisfaction without a doubt, skydeck is fun, trolley experience is great not to mention the very knowledgable tour guide/driver, and the architectural cruise tour is very interesting... i would recommend this package to every tourist

Susan E

5 star rating: Highly Recommended September 2016

Great way to get the Chicago experience and learn about the history of Chicago. I especially enjoyed the architecture cruise. Very relaxing, educational, and the sights were beautiful.

Philip S

5 star rating: Highly Recommended September 2016

Great views and the glass pods were A

Sasha E

5 star rating: Highly Recommended September 2016

Unfortunately the weather didn't cooperate with us on the Skydeck tour but we were offered a chance to move our ticket to another day. Went still went up and had the whole deck to ourselves and saw some sights when the clouds broke. The highlight of this package was the river cruise with Jim. You could feel his passion for the City and architecture in general and he had some great puns.


5 star rating: Highly Recommended September 2016

Very nice variety, the view was beautiful from the Willis Tower Skydeck. Early admission beats the hours long wait. The trolley city tour covered most of the area and well worth the time. Chicago River cruise was very enjoyable and the guide was especially knowledgable. His true love of the city really apparent.

5 star rating: Highly Recommended August 2016

EPIC tour. Early access to Skydeck is a MUST if you're visiting CHI. The trolley tour was a little bit of a let down, but only because if started raining hard. It was still very informative and we made multiple stops for pictures. The river architecture tour is an absolute must. GREAT tour guide, booze on the boat, and amazing architecture. I could definitely do the river architecture tour again.


5 star rating: Highly Recommended August 2016

This tour was a great way to see Chicago -- we only had one day and this tour was perfect for us. Unfortunately, it was raining and poor visibility for the Willis Tower -- however, they were nice enough to allow us to come back the next morning when it was sunny. I cannot stress enough how awesome the VIP package is for Willis Tower -- it's definitely the way to go! Chicago has a lot of great architecture, so the trolley ride and river cruise are both excellent ways to see and hear about all of the amazing buildings in the city. Also, there is plenty of time to get a bite to eat and ride the huge Ferris wheel at the Navy Pier.

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