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    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Sailing
    5. /Chicago Sunset Skyline Sail From Navy Pier
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    Chicago Sunset Skyline Sail From Navy Pier

    Sail Lake Michigan for sweeping views of Chicago’s skyline

    4.6 stars• 646 reviews

    Duration

    75 minutes

    Includes

    Lake Michigan sail, skyline views

    Highlights

    Step aboard Tall Ship Windy for a leisurely sail on Lake Michigan. Explore Chicago’s shoreline and see the city from the water.

    • Take in views of Chicago’s skyline
    • Explore Lake Michigan aboard a sailing vessel
    • Discover Chicago’s shoreline from the water
    • Enjoy an outdoor sailing adventure

    Important details

    • Arrive at least 30 minutes before departure
    • Basic health and mobility are required
    • Requires walking up and down 6 steps
    • Wheelchairs and rolling walkers cannot be used aboard
    • Restricted mobility limits access to the main deck only
    • A credit-card processing fee applies in addition to the listed price; amount not provided

    Cancellation Policy

    All sales are final. Sails operate rain or shine. No-shows are not eligible for rescheduling or refunds. Arrive at least 30 minutes before departure or risk forfeiture.

    Product ID: VK6USR

    FAQs

    You must be able to walk up and down 6 steps. Wheelchairs and rolling walkers cannot be used aboard, and guests with restricted mobility are limited to the main deck for safety.

    The sail operates rain or shine, though the captain may postpone departure for up to 15 minutes during passing inclement weather.

    A credit-card processing fee applies. Clarify the amount with Greetwell before booking.

    Meeting details

    Tall Ship Windy, South Dock, Navy Pier, 600 East Grand Avenue, Chicago, IL 60611

    Experience provided by Tall Ship Windy

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult Ticket

    $63.57

    Ages 13+

    0

    Child Ticket

    $45.95

    0 to 12 years of age - Adults must be selected first

    0

    Infant Ticket

    $16.75

    0 to 12 months of age - Adults must be selected first

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 4
    5/5

    Fun friendly staff!. Had a great sail. Family owned. Good time.

    Photo of jeremiah quinn

    jeremiah quinn

    August 30, 2026

    Review 1 of 1
    5/5

    Fun friendly staff!. Had a great sail. Family owned. Good time.

    Photo of jeremiah quinn

    jeremiah quinn

    August 30, 2026

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