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Chicago Highlights Walking Tour with Skydeck & Cruise

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$189.00 /person
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About the activity

Explore the highlights of Chicago on a guided tour that includes a stroll around town as well as a boat cruise on the Chicago River.

  • Free cancellation
    Cancel up to 24 hours in advance for a full refund.
  • Instant confirmation & Mobile tickets
    Receive your ticket right away. Use your phone or print your voucher.
  • Skip the line
    Get priority entry.
  • Live guiding
    English
  • Duration
    4 hours
  • Includes
    • Visit Skydeck Chicago (Admission Included)
    • Chicago Shoreline Architecture Cruise (Admission Included)
    • Millenium Park to see Cloud Gate Sculpture and Crown Fountain
    • Visit Navy Pier
    • Small group (max 12 people)
    • Gratuities (optional)
Highlights & Description

Highlights

  • Skydeck Admission (Included in Price)
  • Chicago Shoreline Cruise Admission (Included in Price)
  • Cross DuSable Bridge & See Millennium Park, Cloud Gate, and More
  • Small Group Format (Max 12 People)
  • Fully Narrated Walking Tour By A Local Guide

Description

Experience the best of Chicago by day on this small-group tour featuring iconic landmarks, stunning architecture, and a scenic river cruise. Start at Willis Tower, ascending to the Skydeck for panoramic 360° views of the city stretching across 50 miles and four states. Then, stroll through the streets with your expert guide, discovering architectural treasures including the Rookery Building, Marquette Building, Palmer House, Sullivan Center, and Reliance Building.

Pause at Millennium Park to admire the reflective Cloud Gate (“The Bean”), ideal for photos. Cross the historic DuSable Bridge and enjoy the lively Chicago Riverwalk, taking in landmarks such as the Wrigley Building and Tribune Tower. At Navy Pier, board the Shoreline Architecture Cruise to glide past over 40 famous landmarks while learning the fascinating stories behind Chicago’s skyline.

This daytime walking and river tour provides a personalized, small-group experience perfect for architecture enthusiasts, history buffs, or anyone wanting a memorable tour of the Windy City. Enjoy incredible city views, rich stories, and countless photo opportunities—all in one immersive adventure.

Good to know before you go
  • Exact tour length may vary slightly depending on individual walking speeds
  • Tour will operate rain or shine.
  • We recommend dressing for the weather and comfortable footwear. You may also wish to bring water
  • Please arrive at the meeting location 10 mins prior to the start time of the tour
  • Attractions operations may change based on seasonality
Meeting point

Reviews & Ratings

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Frequently Asked Questions

1. What is the cancellation policy for this activity?
Cancel up to 24 hours in advance for a full refund.
2. When will I receive the confirmation of my booking?
You will receive an email notification right after your successful payment. If you don't see it in your inbox, check your spam or junk mail folder. When the payment is completed you have the option to download your ticket directly.
3. What does the 'skip the line' ticket mean?
'Skip the line' tickets provide the fastest possible entry with no or very little queuing.
4. Are mobile tickets enough or do I have to print them?
Tickets don't need to be printed. You can show your ticket from your smartphone as a PDF.
  • Adults
    13-99 years
  • Children
    4-12 years
  • Infants
    0-3 years
April 2026
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