Chicago Night Driving Tour with Skydeck and River Cruise - Image 1
Chicago Night Driving Tour with Skydeck and River Cruise - Image 2
Chicago Night Driving Tour with Skydeck and River Cruise - Image 3
Chicago Night Driving Tour with Skydeck and River Cruise - Image 4
Chicago Night Driving Tour with Skydeck and River Cruise - Image 5
Chicago Night Driving Tour with Skydeck and River Cruise - Image 6

Chicago Night Driving Tour with Skydeck and River Cruise

Explore Chicago's iconic landmarks by night with a driving tour, Skydeck visit, and river cruise, complete with hotel pick-up and drop-off.

Chicago
3 hrs 30 min
4.34Rating:
Last updated: December 7, 2025

Provider Score Distribution

Cumulative distribution showing how many tours score at or below each rating on each provider platform in Chicago.

Platform Scores

GYG logo
4.34
44 reviews
Viator logo
4.35
26 reviews

Important Information

  • Wheelchair accessible
  • Infants and small children can ride in a stroller
  • Service animals allowed
  • Public transportation options nearby
  • Suitable for all physical fitness levels

Experience the magic of Chicago at night with a comprehensive driving tour that includes visits to the city's most iconic landmarks. Begin your adventure at the Willis Tower Skydeck, where you'll ascend to the 103rd floor for breathtaking 360-degree views that stretch across four states. Feel the thrill as you step onto The Ledge, a glass balcony offering a unique perspective of the city lights below. Continue your journey with a relaxing Chicago River cruise, marveling at the illuminated skyline and over 40 architectural landmarks. Conclude your tour with a visit to Millennium Park's Cloud Gate, affectionately known as 'The Bean.' With luxury transportation and a small group setting, this tour provides an intimate and unforgettable way to explore the Windy City. Book now to discover Chicago's vibrant nightlife and stunning architecture.

Pros

  • Admire panoramic views from the Skydeck
  • Cruise the Chicago River at night
  • Explore iconic landmarks like Cloud Gate
  • Enjoy a narrated small-group tour
  • Experience Chicago's skyline illuminated
  • Travel comfortably in luxury transportation

Includes

  • Complimentary hotel pick-up and drop-off in Downtown Chicago
  • Guided driving tour of Chicago
  • Chicago River cruise (admission included)
  • Skydeck admission included
  • Vehicle transportation around multiple points of interest

Excludes

  • Gratuities (optional)
  • Food and beverages not included
$189-$204
4.34Rating:

Tour Highlights

  • Admire panoramic views from the Skydeck
  • Cruise the Chicago River at night
  • Explore iconic landmarks like Cloud Gate
Book on Viator Book on GYG

You'll be redirected to the tour operator's website to complete your booking.

Book on: