Chicago: Night Tour with Willis Tower Entry & Skyline Cruise

4.5 / 5

14 reviews

Activity provider: See Sight Tours USA

Chicago: Night Tour with Willis Tower Entry & Skyline Cruise

Activity provider: See Sight Tours USA
Likely to sell out

From US$ 149 per person

Likely to sell out

Experience the Windy City's most prominent sites on this night tour. Watch the Buckingham Fountain night light show, enjoy a Chicago skyline cruise, and go to the top of the iconic Willis Tower.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Reserve now & pay later
Keep your travel plans flexible—book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures apply. Learn more
Duration 3 hours
Check availability to see starting times.
Skip the line through a separate entrance
Live tour guide
Small group
Limited to 7 participants


  • Experience a feast for the eyes at the Buckingham Fountain light and music show
  • Take in the Chicago city skyline from a unique perspective on a boat cruise
  • Skip the long lines and head straight to the top of the Willis Tower Skydeck
  • Tick Chicago's most iconic landmark, the Chicago Bean, off your bucket list
  • Feel the adrenalin pumping through your veins and admire the city from The Ledge
Full description

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan illuminated at night on this city tour. Enjoy convenient hotel pickup and drop-off, skip-the-ticket-line entry to Willis Tower, and a scenic Chicago skyline cruise.

After getting picked up from your Downtown Chicago hotel, hop in your air-conditioned Mercedes Metris vans and travel to your first stop, Willis Tower, the tallest building in the Western Hemisphere.

Take the elevator all the way up to the 103rd floor of the tower, where you can enjoy 360-degree views spanning 50 miles and 4 states. Get your adrenaline pumping at The Ledge – a glass balcony extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience. Once your feet are back on solid ground, take to the water for a skyline cruise to see the beauty of Chicago's world-famous skyscrapers lit up by the moonlight and bustling city lights. Enjoy a narrated boat tour passing by over 40 Chicago iconic landmarks. End the night by immersing your senses in a spectacular light and music display at Buckingham Fountain – one of the largest fountains in the world. You will also get to see the infamous Chicago Bean (also known as Cloud Gate), Anish Kapoor’s first public outdoor work installed in the United States. At the end of your tour, your guide will take you back to your downtown Chicago hotel.

  • Local tour guide
  • Hotel pickup and drop-off
  • Transportation in an air-conditioned Mercedes Metris van
  • Chicago Skyline cruise
  • Skip-the-ticket-line entry to Willis Tower
  • Tips
  • Food and drinks
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned

Select participants and date



Customer reviews

Overall rating

4.5 /5

based on 14 reviews

Review summary

  • Guide
  • Transportation
  • Value for money

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Our night tour was the BEST! Our guide, Muhammad, was extremely personable, knowledgeable and shared so much history and interesting facts about Chicago. It was great to not have to drive or Uber to 4 different places. We had time to look around every stop and just hopped back in van for next adventure. We were a bit Leary at first but I would TOTALLY recommend this to anyone. We’re still talking wall we got to see and do in one evening. Thanks

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July 6, 2022

Everything moved along swiftly, but wasn’t rushed. All of the ticketing was handled by the guides, so it was super-easy. They managed to keep us on schedule and got us to and from the different points of interest while making sure we were informed about the history of things along the way. Recommended!

June 29, 2022

Danny was great!

July 13, 2022

Product ID: 417359