Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Chicago…
    3. /Water Activities
    4. /Sailing
    5. /Chicago Sunset Skyline Sail From Navy Pier
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Gallery image
    Gallery image 2
    Gallery image 3

    Chicago Sunset Skyline Sail From Navy Pier

    Sail Lake Michigan for sweeping views of Chicago’s skyline

    4.6 stars• 624 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

    We were on the Windy for 2026 4th of July fireworks. Great experience with a friendly and skilled crew. We will likely be back for future events.

    Photo of Eddie

    Eddie

    July 6, 2026

    Review 1 of 1
    5/5

    We were on the Windy for 2026 4th of July fireworks. Great experience with a friendly and skilled crew. We will likely be back for future events.

    Photo of Eddie

    Eddie

    July 6, 2026

    Nearby activities

    Chicago Blues Concert Sail From Navy Pier
    Concert and Special Events

    Chicago Blues Concert Sail From Navy Pier

    Sail Lake Michigan with live blues from Michael Charles and his band

    Sail Lake Michigan with live blues from Michael Charles and his band
    4.6 • 624 reviews
    $76/ person
    Chicago Sunset Skyline Sail
    Sailing

    Chicago Sunset Skyline Sail

    See Chicago’s skyline from Lake Michigan on an evening sail

    See Chicago’s skyline from Lake Michigan on an evening sail
    4.6 • 624 reviews
    $16/ person
    Chicago Navy Pier Fireworks Cruise
    Sailing

    Chicago Navy Pier Fireworks Cruise

    Watch Navy Pier fireworks from the water with Chicago skyline views

    Watch Navy Pier fireworks from the water with Chicago skyline views
    4.6 • 624 reviews
    $108/ person
    Navy Pier Fireworks Cruise in Chicago
    Boat Tours

    Navy Pier Fireworks Cruise in Chicago

    90-minute group sail for Navy Pier fireworks and Chicago skyline views

    90-minute group sail for Navy Pier fireworks and Chicago skyline views
    4.6 • 624 reviews
    $98/ person
    Chicago 4-Hour Bareboat Charter
    Yacht Charters

    Chicago 4-Hour Bareboat Charter

    Design your own Chicago lakefront day aboard Soulshine

    Design your own Chicago lakefront day aboard Soulshine
    $2,070& up
    Chicago Yamaha FX Cruiser Jet Ski Rental
    Jet Skiing

    Chicago Yamaha FX Cruiser Jet Ski Rental

    Ride a new 2026 Yamaha cruiser along Chicago's lakefront

    Ride a new 2026 Yamaha cruiser along Chicago's lakefront
    $374/ jet ski