Chicago Private Sailing on Lake Michigan 2 hr - Image 1
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Chicago Private Sailing on Lake Michigan 2 hr

TourTruth score 8.9 out of 10

Very goodTop 6% in Chicago

73 reviews · Rated on 1 provider · How we score

  • Chicago
  • 2 hrs
  • Updated November 2, 2026

Sail Lake Michigan on a private Chicago charter for up to six, with skyline views and a captain who can share local stories.

About this tour

Set sail from Navy Pier and see Chicago from the open water on a private Lake Michigan charter. For two hours, a US Coast Guard-licensed captain guides your group along the lakefront, with the city skyline rising above the shore.

Make the outing your own: bring up to six guests, choose your music, and customize the sailing route. This is a relaxed private sail rather than an in-depth guided tour, but the captain is happy to point out notable sights and share local history when asked. Bluetooth speakers are available, and you can select from three daily departure times.

Meet outside Navy Pier Marina at Gate D on the pier’s north side and contact the crew for an escort to the boat. Food and drinks are not included, so plan accordingly and follow the onboard rules. Book your Chicago private sailing experience for a fresh perspective on the city and its lakefront.

Highlights

  • Sail along Chicago’s lakefront aboard a private charter
  • Admire skyline views with a licensed captain at the helm
  • Choose your guest list, music, and sailing route
  • Ask the captain about local sights and history

What's included

Included

  • Use of Bluetooth speakers
  • Navy Pier facility fee
  • All taxes
  • Professional US Coast Guard-licensed captain

Not included

  • Gratuities
  • Food and drinks
  • Parking

Ratings on each provider

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

Important information

  • Meet outside Navy Pier Marina at Gate D on the north side of Navy Pier, then call or text to be escorted to the sailboat
  • Late arrival may shorten the charter without a refund or price adjustment
  • Smoking and tobacco products, including e-cigarettes and vapor devices, are prohibited
  • Glass containers are prohibited; wine and Champagne bottles must remain secured in a protective container
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  • Alcohol may be consumed in reasonable amounts within Illinois law
  • Animals and weapons are prohibited
  • Swimming may be permitted on charters of 3 hours or longer at the captain’s discretion; it is not guaranteed
  • The captain may cancel for weather, mechanical failure, or safety; the charter will be rescheduled or refunded if rescheduling cannot be agreed upon
  • Guests who board consent to being filmed, photographed, and recorded for promotional use without compensation

How this score is calculated

This score is based on one provider. Viator rates it 5.00 from 73 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 8.9. Top 6% in Chicago means it ranks in the top 6% of tours in Chicago by this score.

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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