Chicago Skyline Sail 75 min - Image 1
Chicago Skyline Sail 75 min - Image 2
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Chicago Skyline Sail 75 min

TourTruth score 6.8 out of 10

Average

32 reviews · Rated on 1 provider · How we score

  • Chicago
  • 1 hr 15 min
  • Updated November 2, 2026

Sail Lake Michigan aboard Tall Ship Windy, help raise a sail or relax on deck, and take in views of the Chicago skyline.

About this tour

See Chicago from the water on a relaxing sail aboard Tall Ship Windy, the city’s Official Tall Ship Ambassador. This 75-minute Chicago Skyline Sail takes you onto Lake Michigan for fresh air and views of the skyline from the deck of a tall ship.

Join the friendly crew to help raise one of Windy’s sails, or settle in and let others handle the work. The experience is described as fun for all ages, with a full bar and gift shop on board. A restroom is also available during the sail.

Meet near Billy Goat Bar and Grill to board Tall Ship Windy. Whether you want to lend a hand with the sails or simply enjoy the lake breeze and city views, this Chicago Skyline Sail offers a memorable way to spend time on the water. Book your sail and see the city from a fresh perspective.

Highlights

  • Sail Lake Michigan aboard Tall Ship Windy
  • Admire views of the Chicago skyline from the water
  • Help the crew raise a sail or relax on deck
  • Enjoy fresh air aboard Chicago’s Official Tall Ship Ambassador

What's included

Included

  • Restroom on board

Not included

  • Alcoholic beverages
  • Snacks
  • Gratuities

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

Important information

  • Service animals are allowed
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • Departure point: Tall Ship Windy, near Billy Goat Bar and Grill

How this score is calculated

This score is based on one provider. Viator rates it 4.72 from 32 reviews. We place that rating among all Viator ratings and weight it by its review count. If the tour is found on another provider later, both ratings are combined.

How the score works and rating distribution in Chicago
  • Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
  • Listings on different providers are combined in proportion to their review counts.
  • Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
  • The result is shown from 0 to 10: this tour scores 6.8.

Provider rating distribution in Chicago

How many tours in Chicago have a provider rating at or below each value. The dashed line is this tour.

  • GetYourGuide
  • Viator

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