Chicago Night Driving Tour with Skydeck and River Cruise



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.

Highlights

  • Skydeck Admission (Admission Included)
  • Chicago Shorline Cruise (Admission Included)
  • Complimentary Hotel Pick-Up and Drop-Off in Downtown Chicago
  • Small Group Narrated Driving Tour (Max 6 People)
  • See famous landmarks including Cloud Gate (“The Bean”)

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, 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.

Includes

Scenic Chicago Cruise (Admission Included) Chicago SkyDeck (Admission Included) Hotel pickup and drop-off Anywhere Downtown Chicago Narrated Guided Tour of Chicago City Vehicle Transportation around multiple points of interest in Chicago

Easy cancellation

Cancel up to 24 hours in advance for a full refund

Available Dates

March 2026 31 dates
Sun 1st Mar Mon 2nd Mar Tue 3rd Mar Wed 4th Mar Thu 5th Mar Fri 6th Mar
April 2026 30 dates
Wed 1st Apr Thu 2nd Apr Fri 3rd Apr Sat 4th Apr Sun 5th Apr Mon 6th Apr
May 2026 31 dates
Fri 1st May Sat 2nd May Sun 3rd May Mon 4th May Tue 5th May Wed 6th May
June 2026 30 dates
Mon 1st Jun Tue 2nd Jun Wed 3rd Jun Thu 4th Jun Fri 5th Jun Sat 6th Jun
July 2026 31 dates
Wed 1st Jul Thu 2nd Jul Fri 3rd Jul Sat 4th Jul Sun 5th Jul Mon 6th Jul
August 2026 4 dates
Sat 1st Aug Sun 2nd Aug Mon 3rd Aug Tue 4th Aug

We Are Part of the My Guide Network!

My Guide Chicago is part of the global My Guide Network of Online & Mobile travel guides. We are now in 180+ Destinations and Growing.

Nearby Destinations