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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!

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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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Option A
  • 8am: Access to the Skydeck 
  • 9:15am: Board the trolley for a 2-hour city tour
  • 11:15am: Arrive at Navy Pier 
  • 1pm: Architecture cruise

Option B
  • 8:30am: Access to the Skydeck
  • 9:45am: Board the trolley for a 2-hour city tour
  • 11:45am: Arrive at Navy Pier
  • 1pm: Architecture cruise

Customer Reviews

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.

Linda M

5 star rating: Highly Recommended August 2016

Great Chicago experience. Trolley driver Ulysess and the cruise guy sorry I forgot his name who did the architect tour was very knowledgeable and made our boat ride informative and enjoyable.

paula b

5 star rating: Highly Recommended August 2016

Loved this tour! Was very enjoyable and informative. Highlight of our stay in Chicago.

Roger S

5 star rating: Highly Recommended July 2016

A great three part tour - the Willis Tower with the sky deck private access , the trolley tour of the highlights of the city a nice overview, and the Chicago river cruise in and out of the city between the various buildings like a modern day Venice is a must!!! An over all great tour and highly recommended!!!

Patricia N

5 star rating: Highly Recommended July 2016

Loved this tour especially the Willis Tower, the early access meant that we were the only people in the Skydeck and there was 5 of us so we had the whole floor to ourselves plus the guide who was great and very knowledgeable. The views from the Skydeck were amazing, most of us got very daring and walked out onto the glass platforms so great photo opportunities.
The City Trolley tour was a bit different but we did get to see lots of the historic places of Chicago. We were then taken to the Navy Pier in time to get some lunch before boarding the boat and the River Cruise again a very knowledgeable guide and a great tour.

Alexa B

5 star rating: Highly Recommended July 2016

This tour was amazing!


5 star rating: Highly Recommended July 2016

Early access to Willis Tower and the Skydeck says it all. This can be over an hour if you wait too long.
Step out onto the Skydeck to see what 412m 1,353' of just glass under your feet looks, and feels, like.
The trolley tour gives you a couple of hours driving 'round the Windy City with a good commentary.
The cruise is great as they cover the city's architecture over the years. However it is not a small group tour as with the Willis Tower and Trolley bus tour. Here you are packed on to a boat with a whole pile of people who may not understand what sitting down means.
Note: The location for the cruise is not at the ferry wharf, but on the river before you get to Navy Pier, off North Streeter Drive the Western half on the Lakefront Trail, and you have to exchange your voucher on Navy Pier on the South side at the Shoreline Sightseeing kiosk.

Scott C

5 star rating: Highly Recommended July 2016

Very fun and informative tour around Chixago. Getting on the Willis sky deck before the general public is worth it alone. The river tour guide was excellent.

Lizbeth M

5 star rating: Highly Recommended July 2016

This tour was amazing!

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