Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise

42 Reviews
Tours Good for groups For returning travelers Reseller exclusions Sightseeing Tours Theme Tours Cruises & boat tours Small group Medium-risk activities

Experience Chicago's most prominent sights on this night tour with hotel transfers. Enjoy a skyline cruise of the Windy City, and head to the top of the Skydeck observation deck at Willis Tower.


  • Feel the adrenaline pumping through your veins from the 103rd floor of a tower
  • Take in the Chicago city skyline from a unique perspective on a boat cruise
  • Get your adrenaline pumping at The Ledge
  • Tick Chicago's most iconic landmark, the Chicago Bean, off your bucket list
  • See the Windy City's skyscrapers lit up by the moonlight on the skyline cruise


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, entry to Willis Tower, and a scenic Chicago skyline cruise. After getting picked up from your Downtown Chicago hotel, hop in your Mini van 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 boat tour passing by over 40 Chicago iconic landmarks. 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 Mini van Scenic cruise Skip-the-line entry to Willis Tower

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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