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Chicago Sunset Sail on Lake Michigan

Sail into the sunset on Lake Michigan with a private charter, enjoying Chicago's skyline and a personalized experience with a licensed captain.

Chicago
2 hrs
4.56Rating:
1 provider liveLast updated: April 7, 2026

Provider Score Distribution

Cumulative distribution showing how many tours score at or below each rating on each provider platform in Chicago.

Provider Scores

Viator logo
4.96
27 reviews

Important Information

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • No smoking; all charters are non-smoking
  • Alcohol allowed within Illinois State law
  • No glass containers; bring plastic cups

Experience the magic of a Chicago Sunset Sail on Lake Michigan, where the city skyline meets the serene waters. This private two-hour sailing adventure is perfect for up to six guests, offering a personalized experience with a US Coast Guard licensed captain at the helm. As you glide along the lakefront, enjoy the flexibility to tailor your journey, from the music you play to the route you take. Capture the breathtaking views of Chicago's iconic skyline as the sun sets, creating a picturesque backdrop for your sail. Whether you're looking to relax or celebrate a special occasion, this sunset sail promises an unforgettable evening. Book your Chicago Sunset Sail on Lake Michigan today and create lasting memories.

Pros

  • Sail along Chicago's stunning lakefront
  • Relax with a private charter experience
  • Customize your music and route
  • Admire the iconic city skyline
  • Enjoy a licensed captain's expertise
  • Capture breathtaking sunset views

Includes

  • Use of Bluetooth speakers
  • Professional captain licensed by the US Coast Guard
  • Navy Pier Facility Fee
  • All taxes

Excludes

  • Gratuities
  • Food and drinks (you may bring your own)
  • Parking

FAQ

  • What Is the Maximum Group Size?

    The maximum group size for this sail is six people.

  • Can We Bring Our Own Food and Drinks?

    Yes, you may bring your own food and drinks on board.

  • Is There a Restroom on the Boat?

    Yes, there is a restroom available on the sailboat.

  • What Happens in Case of Bad Weather?

    Charters may be rescheduled or refunded due to weather.

  • Are Pets Allowed on Board?

    Unfortunately, pets are not allowed on this sail.

$507.96
4.56Rating:

Tour Highlights

  • Sail along Chicago's stunning lakefront
  • Relax with a private charter experience
  • Customize your music and route
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