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Chicago City Highlights: Small-Group Guided Tour with Entrance + Transfer

Explore the best of the Windy City with a guided small group tour

Duration: 4h
Live guide: English
Max group size: 6
Provider: TripShepherd USD
Registered address: 4673 Ontario Ave, Suite 203, L2E 3R1, Niagara Falls, US
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4-hour guided tour of Chicago
Expert guide
Small group setting (max. 6 people)
Admission to the Skydeck Chicago Observatory
Admission to Shoreline Architecture Cruise
Hotel pickup and drop-off
Guide gratuities
Food and drink
Admission to attractions and monuments not listed
  • Meet your guide at the Willis Tower 238 E Monroe St, Chicago, IL 60601
  • Show your smartphone ticket to your guide at the start of the tour
  • Hotel pick-up is also available for this tour; please include your hotel address during checkout if you would like to be picked up at your accommodation

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan with tickets for a guided tour of Chicago's highlights.

In a small group setting, you'll have access to your own local expert and personal guide to share unique and fascinating stories about the surrounding area, including exclusive insights, historic highlights, and personalized recommendations.

No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere – Skydeck Chicago (formerly Sears Tower). Take the elevator all the way up to the 103rd floor and experience a spectacular 360-degree view spanning 50 miles and four states.

Once your feet are back on solid ground, your guide will take you to the Adler Planetarium Pier, a must-see while in the Windy City.

Hop aboard the Shoreline Architecture Cruise, a narrated boat tour that takes you past over 40 Chicago iconic landmarks, from hidden architectural features to Chicago's most famous monuments – including Buckingham Fountain and the Chicago Bean.

  • Cancellation is possible until 24 hours before your visit.
  • Rescheduling is possible until 24 hours before your visit.

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