Best of Chicago: Skydeck, River Cruise & City Walking Tour

Activity provider: Walks - US

Best of Chicago: Skydeck, River Cruise & City Walking Tour

Activity provider: Walks - US

From US$ 125 per person

Experience the very best of Chicago. Start your day with first-entry tickets to the Skydeck for stunning views. Explore downtown Chicago on a guided walking tour, then relax on a 1.5-hour cruise.

About this activity

Free cancellation
Cancel up to 24 hours in advance for 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 are in place. Check your activity voucher once you book for full details.
Duration 2 hours
Check availability to see starting times.
Live tour guide
Wheelchair accessible


  • Take the first elevator of the day up to the Skydeck.
  • Explore Chicago’s Art Deco architecture.
  • Discover details only an expert knows to look for.
  • See the largest Tiffany glass dome in the world.
  • Enjoy a 90-minute architecture river cruise.
Full description
At Willis Tower, take the first elevator of the day up 103 floors to the Skydeck, the 3rd tallest building in the Western Hemisphere. On a clear day views extend to 4 States!! Back on ground level, it’s time to traverse Chicago’s Loop, alongside your local guide and see the city’s Art Deco architecture will be laid out before – or rather, above – you! Pass the magnificent Board of Trade Building and take in the statue of Ceres, Ancient Greek goddess of the harvest, looming over the skyline three stories high. The Loop may be a business district but it’s much more than that—including the birthplace of the world’s first skyscraper. At the Monadnock Building where your expert local guide will be waiting to take you on a journey through the city’s most storied structures Next, walk through the awe-inspiring lobby designed by Frank Lloyd Wright at the Rookery. Many elements here only an expert can point out, including the secret glass mosaics adorning the lobbies. You’ll listen to the history of the cast of characters that brought Chicago to world-wide fame, admire one of the world’s most historically significant doors and get a view of the largest Tiffany glass dome in the world. Millennium Park is the next stop where the iconic Cloud Gate can be found. After getting a picture in front of ‘The Bean’, it’s time to walk up Michigan Avenue for more architectural stories and history. The last stop of the day is Chicago’s iconic Riverwalk for a 90-minute architecture cruise, passing down the Chicago River and Lake Michigan. Enjoy the snacks and refreshments available to purchase on board, and take in the day’s discoveries from the water.
  • Local English-speaking guide
  • Expertly guided walking tour
  • Hotel pickup and drop-off
  • Gratuities

Select participants and date



Meeting point

Meet in front of the coffee shop called Inteligencia. The tour meeting time is 15 minutes prior to the tour start time. Your guide will be holding a Walks sign.

Open in Google Maps ⟶
Important information

Know before you go

  • All sites are visited from the exterior unless otherwise noted
  • Guests should be able to walk at a moderate pace without difficulty
  • The tour partner complies with all local government regulations. You may need to wear a mask or provide proof of vaccination to enter certain venues. Please refer to Chicago government guidelines for the most up-to-date information.
Customer reviews

Overall rating

5 /5

based on 5 reviews

Sort by:

Traveler type:

Star rating:

We are entitled to a beautiful walking tour through the streets of Chicago with Raquel, a fantastic guide. Our experience was really very interesting and really well guided with a very dynamic and human person. Since the boat trip included in the visit had been canceled (and refunded) we were treated to a really interesting and more relaxed tour. We weren't in a hurry and were able to take advantage of this beautiful activity which was done more in "slow motion". Thank you Raquel for a great tour that I would recommend to everyone when you arrive in Chicago.

Read more

November 6, 2022

Good guide Saturday is a good day for the tour there are no people and you can better appreciate the Architecture of Downtown Chicago and walk very calmly, unlike on weekdays through the large corporate offices, government agencies, Federal State Courts, etc. that are working

June 20, 2022

Super! Visite très intéressante

November 4, 2022


Product ID: 401807