
Scenic Chicago Night Tour
11 top attractions · 3.5 hours · tickets & logistics handled
Scenic Chicago Night Tour is curated for guests who want to discover Chicago’s charm after dark.
What You'll Experience
- Experience The Ledge, a glass balcony extending 1,353 feet above ground for a thrilling perspective
- Visit to Skydeck Chicago at Willis Tower with panoramic 360-degree views across 4 states
- Relaxing Shoreline Architecture Cruise passing by more than 40 iconic buildings lit up along the Chicago River
- Stop at Cloud Gate (The Bean), Anish Kapoor’s reflective sculpture in Millennium Park
We handle everything
Pickup & drop-off
Your guide will pick you up and drop off at your downtown Chicago hotel.
Tickets
Included for 2 attractions
Timing
Back in 3.5 hours
What you'll see
Everything inside your CA$237
Booked separately, these are 2 tickets, 2queues, and a day of planning. Here it's one booking.
That's the whole price — no booking fees at checkout.
Excludes
Why We're The Better Choice
- Max 10 GuestsCrowded 50+ seat buses
- Skip Ticket LinesWaiting in ticket queues
- Door-to-Door PickupWalking to meeting points
- Live Local GuideRecorded commentary
Description
Begin your 3 hour small-group Scenic Night Tour of Chicago with complimentary downtown Chicago hotel pick up in the comfort and style of one of our complimentary vehicles where you will be escorted to your very first stop - Willis Tower. No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere - Willis Tower (formerly Sears Tower). Taking the elevator all the way up to the 103rd floor where you will enjoy a dazzling 360-degree view spanning 50 miles and 4 states. The most spectacular view - 1,353 feet down "Dare to Stand Out" on The Ledge - special glass balconies extending 4.3 feet outside the building which provides a thrilling, once-in-a-lifetime experience. Once your feet are back on solid ground your guide will take you on a beautiful skyline cruise to see the beauty of Chicago's architecture lit up by the moonlight and bustling city lights by seeing world-famous skyscrapers from the Chicago River. Aboard the relaxing cruise you will enjoy a boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. To end your night out, You will also get to see the infamous Chicago Bean (also known as Cloud Gate), British 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.
Important Information
Know Before You Book:
- The exact length time for a tour may vary slightly based on traffic and seasonality (during off-peak times, tours tend to be a little shorter due to less traffic.
- The cruise is replaced with a Field Museum during winter.
- The lead traveler’s name is needed for all bookings.
- Full names of all travelers are required when making a reservation.
Know Before You Go:
- Don’t forget to bring a camera and some spending money for souvenirs along the way.
- This tour involves a moderate amount of walking so it’s advisable to wear comfortable walking shoes.
- If we don’t stop at Buckingham Fountain and Adler viewpoint, we will substitute with a luxurious drive up Chicago’s famed Magnificent Mile; including hop-out stops at The Chicago Theatre, the Chicago Picasso sculpture in Daley plaza, and the Chicago Watertower (sole survivor of the Chicago Fire).
- Check the weather forecast and dress appropriately for the conditions
- Pick up time will be confirmed 1-3 days prior to the tour date via email or phone. If you do not have access to these, please be ready 30 minutes before the tour start time in the hotel lobby.
Not Recommended For:
- Individuals with mobility challenges
- Individuals with heart conditions
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Two ways to take this tour
Join a Small Group
CA$237/person · max 10 guests · everything included
Make It Private
reserve the remaining seats at 20% off · your group only · same route, your pace
Change-of-Plans Guarantee
Cancel free up to 24 hours before your tour — full refund, no questions.
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See Sight Tours has been providing travel services across North America since 2006. Operating in 22 cities across Canada and the USA, the company specializes in small group tours that offer personalized, high-quality experiences for travelers.
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- Toll Free1-888-961-6584
- Local1-289-271-9767
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